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73573-88-3

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  • Factory Supply (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl(2S)-2-methylbutanoate

    Cas No: 73573-88-3

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73573-88-3 Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 73573-88-3 differently. You can refer to the following data:
1. A fungal metabolite which is a potent inhibitor of HMG-CoA reductase.
2. Mevastatin (compactin) is a diterpene produced by several species of the genera Penicillium and Monascus, first reported in 1976. Mevastatin, the prtotype of the statin class, is a potent competitive inhibitor of HMG-CoA reductase, a regulatory enzyme for cholesterol biosynthesis. Mevastatin has also been shown to induce apoptosis by inhibiting post-translational prenylation of proteins such as Ras, increasing eNOS mRNA and protein levels by blocking the geranylgeranylation of Rho, and inhibiting myoblast fusion. It induces cell cycle arrest in late G1 phase and may induce bone morphogenic protein-2 (BMP-2).
3. anti-hyperlipoproteinemic, 3-hydroxy-3-methyl glutaryl coenzyme A (HMG-CoA) reductase inhibitor

Definition

ChEBI: A carboxylic ester that is pravastatin that is lacking the allylic hydroxy group and in which the lactone moiety has been hydrolysed to the corresponding delta-hydroxy-carboxylic acid. A hydroxymethylglutaryl-CoA reductase inhibitor (stati ) isolated from Penicillium citrinum and from Penicillium brevicompactum, its clinical use as a lipid-regulating drug ceased following reports of toxicity in animals.

General Description

Chemical structure: statin

Biological Activity

Inhibitor of HMG-CoA reductase; decreases cholesterol biosynthesis, in vitro and in vivo . Induces apoptosis, arrests cancer cells in G1 phase and downregulates cdk 2, 4, and 6, cyclin D1 and E1, p21 and p27.

Biochem/physiol Actions

Mevastatin is a selective inhibitor of 3-hydroxy 3-methyl glutaryl coenzyme(A) reductase (HMG-CoA reductase), a major enzyme involved in cholesterol synthesis. It acts as a cholesterol-lowering agent. Mevastatin is obtained from various species of fungi. It acts as an antiresorptive?agent and has therapeutic effects to treat osteoporosis. Mevastatin inhibits bone resorption by triggering osteoclast apoptosis. It is also involved in the inhibition of prenylation of proteins such as Ras. Mevastatin increases endothelial nitric oxide synthase (eNOS) mRNA and protein levels by blocking the geranylgeranylation of transcription factor Rho.

Purification Methods

Purify compactin by recrystallisation from aqueous EtOH. UV (EtOH): max 230, 237 and 246nm (log  4.28, 4.30 and 4.11); IR (KBr): 3520, 1750 (lactone CO) and 1710 (CO ester) cm-1. [Clive et al. J Am Chem Soc 110 6914 1988, Review: Rosen & Heathcock Tetrahedron 42 4909 1986, IR, NMR, MS: Brown et al. J Chem Soc Perkin Trans 1 1165 1976.] It is a potent inhibitor of 3-hydroxy-3-methylglutaryl-CoA reductase (HMG-CoA reductase), an enzyme in cholesterol biosynthesis, and lowers cholesterol levels [Brown et al. J Biol Chem 253 1121 1978, Nakamura & Ableles Biochemistry 24 1364 1985, Beilstein 18/3 V 145].

references

[1] endo a. the discovery and development of hmg-coa reductase inhibitors. journal of lipid research, 1992, 33(11): 1569-1582.

Check Digit Verification of cas no

The CAS Registry Mumber 73573-88-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,3,5,7 and 3 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 73573-88:
(7*7)+(6*3)+(5*5)+(4*7)+(3*3)+(2*8)+(1*8)=153
153 % 10 = 3
So 73573-88-3 is a valid CAS Registry Number.
InChI:InChI:1S/C23H34O5/c1-4-14(2)23(26)28-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-18-12-17(24)13-21(25)27-18/h6,8-9,14-15,17-20,22,24H,4-5,7,10-13H2,1-3H3

73573-88-3 Well-known Company Product Price

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  • TCI America

  • (M2275)  Mevastatin  >98.0%(HPLC)

  • 73573-88-3

  • 1g

  • 890.00CNY

  • Detail
  • TCI America

  • (M2275)  Mevastatin  >98.0%(HPLC)

  • 73573-88-3

  • 5g

  • 2,990.00CNY

  • Detail
  • Sigma

  • (M2537)  Mevastatin  ≥95% (HPLC), powder

  • 73573-88-3

  • M2537-5MG

  • 1,244.88CNY

  • Detail

73573-88-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name mevastatin

1.2 Other means of identification

Product number -
Other names Compactin (penicillium)

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:73573-88-3 SDS

73573-88-3Synthetic route

(1S,2S,8S,8aR,3'R,5'R,2''S)-methyl 1,2,6,7,8,8a-hexahydro-3',5'-dihydroxy-2-methyl-8-<(2-methyl-1-oxobutyl)oxy>-1-naphthaleneheptanoate
79814-60-1

(1S,2S,8S,8aR,3'R,5'R,2''S)-methyl 1,2,6,7,8,8a-hexahydro-3',5'-dihydroxy-2-methyl-8-<(2-methyl-1-oxobutyl)oxy>-1-naphthaleneheptanoate

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 1.08333h; Ambient temperature;70%
With toluene-4-sulfonic acid In benzene70%
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-[2-((2R,4R)-4,6-dihydroxy-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
116996-42-0, 117065-49-3

(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-[2-((2R,4R)-4,6-dihydroxy-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
With Celite; silver carbonate In toluene at 95℃; for 2h;61%
(1S,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-7-methyl-8-<2-((2R,4R)-tetrahydro-4-methoxy-6-oxo-2H-pyran-2-yl)-ethyl>-1-naphthyl (2S)-2-methylbutyrate
84751-53-1

(1S,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-7-methyl-8-<2-((2R,4R)-tetrahydro-4-methoxy-6-oxo-2H-pyran-2-yl)-ethyl>-1-naphthyl (2S)-2-methylbutyrate

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
With boron tribromide In dichloromethane at -23℃; for 5h;31%
With boron tribromide In dichloromethane at -23℃; for 6h;31%
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
108713-03-7

(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
With hydrogen fluoride In water; acetonitrile at 45℃; for 8h;30%
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
87000-71-3

(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
With hydrogen fluoride In acetonitrile at 25℃; for 0.5h; Yield given;
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-[2-((2R,4R,6S)-4,6-dihydroxy-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
116996-42-0, 117065-49-3

(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-[2-((2R,4R,6S)-4,6-dihydroxy-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
With Celite; silver carbonate In toluene at 95℃; for 2h; Yield given;
3,5-Dihydroxy-7-[(1S,2S,8S,8aR)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-heptanoic acid methyl ester
67383-81-7, 79814-60-1, 79896-19-8, 79896-20-1, 79896-21-2, 109785-25-3, 109785-26-4

3,5-Dihydroxy-7-[(1S,2S,8S,8aR)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-heptanoic acid methyl ester

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene at 25℃; for 0.5h;
(R)-3,5-Dihydroxy-7-[(1S,2S,8S,8aR)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-heptanoic acid methyl ester
67383-81-7, 79814-60-1, 79896-19-8, 79896-20-1, 79896-21-2, 109785-25-3, 109785-26-4

(R)-3,5-Dihydroxy-7-[(1S,2S,8S,8aR)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-heptanoic acid methyl ester

A

mevastatin
73573-88-3

mevastatin

B

3,5-bis-epi-compactin
84173-31-9

3,5-bis-epi-compactin

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene at 25℃; for 0.25h;A 32 mg
B 22 mg
methyl 3,5-dihydroxy-7-<(1'S,2'S,8'S,8a'S)-2'methyl-8'-<(S)-2-methylbutanoyloxy>-1',2',3',7',8',8a'-hexahydro-1'-naphthyl>heptanoate
67383-81-7, 79814-60-1, 79896-19-8, 79896-20-1, 79896-21-2, 109785-25-3, 109785-26-4

methyl 3,5-dihydroxy-7-<(1'S,2'S,8'S,8a'S)-2'methyl-8'-<(S)-2-methylbutanoyloxy>-1',2',3',7',8',8a'-hexahydro-1'-naphthyl>heptanoate

A

mevastatin
73573-88-3

mevastatin

B

3,5-bis-epi-compactin
84173-31-9

3,5-bis-epi-compactin

Conditions
ConditionsYield
With pyridine hydrogenfluoride In acetonitrile at 0℃; for 6h;A 15.6 mg
B 15.4 mg
(4S,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-6-[2-((1S,2S,8aR)-2-methyl-8-triethylsilanyloxy-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl)-ethyl]-[1,3]dioxane
116996-36-2, 117065-47-1

(4S,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-6-[2-((1S,2S,8aR)-2-methyl-8-triethylsilanyloxy-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl)-ethyl]-[1,3]dioxane

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min
2: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
3: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
4: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
5: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
6: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
7: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
8: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 8 steps
1: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min
2: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
3: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
4: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
5: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
6: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
7: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
8: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
4-[(1S,5S,6S)-6-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-5-methyl-2-oxo-cyclohex-3-enyl]-4-triethylsilanyloxy-butyraldehyde
116996-35-1, 117065-46-0

4-[(1S,5S,6S)-6-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-5-methyl-2-oxo-cyclohex-3-enyl]-4-triethylsilanyloxy-butyraldehyde

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h
2: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min
3: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
4: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
5: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
6: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
7: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
8: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
9: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 9 steps
1: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 3 h
2: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min
3: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
4: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
5: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
6: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
7: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
8: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
9: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(4R,6S)-6-(2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
116996-40-8

(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(4R,6S)-6-(2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
2: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
3: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 3 steps
1: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
2: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
3: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(4R,6R)-2,2-dimethyl-6-(2-oxo-ethyl)-[1,3]dioxan-4-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
116996-41-9

(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-{2-[(4R,6R)-2,2-dimethyl-6-(2-oxo-ethyl)-[1,3]dioxan-4-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
2: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 2 steps
1: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
2: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
<4R-<4α*(1R*,2S*)>6α>>-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-α-(2-methyl-5-oxo-3-cyclohexen-1-yl)-1,3-dioxane-4-propanal
116996-31-7, 126060-10-4

<4R-<4α*(1R*,2S*)>6α>>-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-α-(2-methyl-5-oxo-3-cyclohexen-1-yl)-1,3-dioxane-4-propanal

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 50 percent / (Ph3P)3RhCl / toluene; acetonitrile / 2.5 h / Heating
2: 1.) LDA / 1.) Et2O, -78 deg C, 1 h; 2.) -78 deg C, 10 min
3: 96 percent / i-Pr2NH / DMAP / diethyl ether / 36 h / Ambient temperature
4: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C, 20 min, r.t., 8 h
5: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h
6: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min
7: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
8: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
9: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
10: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
11: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
12: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
13: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 13 steps
1: 50 percent / (Ph3P)3RhCl / toluene; benzonitrile / 2.5 h / Heating
2: 1.) lithium diisopropylamide (LDA) / 1.) Et2O, -78 deg C, 1 h, 2.) -78 deg C, 10 min
3: 96 percent / i-Pr2NH, 4-(dimethylamino)pyridine (DMAP) / diethyl ether / 36 h / Ambient temperature
4: 1.) O3, 2.) Ph3P / 1.) CH2Cl2, -78 deg C, 20 min, 2.) RT, 8 h
5: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 3 h
6: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min
7: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
8: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
9: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
10: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
11: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
12: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
13: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
(7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-3,7,8,8a-tetrahydro-2H-naphthalen-1-one
116996-38-4

(7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-3,7,8,8a-tetrahydro-2H-naphthalen-1-one

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
2: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
3: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
4: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
5: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
6: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 6 steps
1: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
2: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
3: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
4: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
5: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
6: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
(4S,5S,6S)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-6-(1-hydroxy-pent-4-enyl)-4-methyl-cyclohex-2-enone
116996-33-9, 117065-44-8

(4S,5S,6S)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-6-(1-hydroxy-pent-4-enyl)-4-methyl-cyclohex-2-enone

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 96 percent / i-Pr2NH / DMAP / diethyl ether / 36 h / Ambient temperature
2: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C, 20 min, r.t., 8 h
3: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h
4: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min
5: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
6: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
7: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
8: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
9: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
10: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
11: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 11 steps
1: 96 percent / i-Pr2NH, 4-(dimethylamino)pyridine (DMAP) / diethyl ether / 36 h / Ambient temperature
2: 1.) O3, 2.) Ph3P / 1.) CH2Cl2, -78 deg C, 20 min, 2.) RT, 8 h
3: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 3 h
4: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min
5: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
6: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
7: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
8: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
9: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
10: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
11: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
116996-39-5

(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
2: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
3: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
4: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 4 steps
1: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
2: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
3: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
4: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
(4S,5S,6S)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-4-methyl-6-(1-triethylsilanyloxy-pent-4-enyl)-cyclohex-2-enone
116996-34-0, 117065-45-9

(4S,5S,6S)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-4-methyl-6-(1-triethylsilanyloxy-pent-4-enyl)-cyclohex-2-enone

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C, 20 min, r.t., 8 h
2: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h
3: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min
4: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
5: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
6: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
7: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
8: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
9: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
10: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 10 steps
1: 1.) O3, 2.) Ph3P / 1.) CH2Cl2, -78 deg C, 20 min, 2.) RT, 8 h
2: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 3 h
3: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min
4: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
5: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
6: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
7: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
8: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
9: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
10: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
<4R-<4α(4R*,5R*),6α>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-one
116996-32-8

<4R-<4α(4R*,5R*),6α>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-one

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 1.) LDA / 1.) Et2O, -78 deg C, 1 h; 2.) -78 deg C, 10 min
2: 96 percent / i-Pr2NH / DMAP / diethyl ether / 36 h / Ambient temperature
3: 1.) O3; 2.) Ph3P / 1.) CH2Cl2, -78 deg C; 2.) -78 deg C, 20 min, r.t., 8 h
4: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h
5: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H2O, MeCN, r.t., 1.75 h; 2.) CH2Cl2, 0 deg C, 40 min
6: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
7: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
8: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
9: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
10: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
11: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
12: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 12 steps
1: 1.) lithium diisopropylamide (LDA) / 1.) Et2O, -78 deg C, 1 h, 2.) -78 deg C, 10 min
2: 96 percent / i-Pr2NH, 4-(dimethylamino)pyridine (DMAP) / diethyl ether / 36 h / Ambient temperature
3: 1.) O3, 2.) Ph3P / 1.) CH2Cl2, -78 deg C, 20 min, 2.) RT, 8 h
4: 85 percent / C8K, TiCl3 / 1,2-dimethoxy-ethane / 1.) RT, 5 h, 2.) reflux, 3 h
5: 1.) 48percent aq. HF, 2.) 2-methoxypropene, pyridinium p-toluenesulfonate / 1.) MeCN, RT, 1.75 h, 2.) CH2Cl2, 0 deg C, 40 min
6: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
7: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
8: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
9: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
10: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
11: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
12: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
(7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-ol
116996-37-3, 117065-48-2

(7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-ol

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1.) (COCl)2; 2.Et3N / 1.) DMSO, CH2Cl2, -78 deg C, 15 min; 2.) -78 deg C, 5 min
2: 80 percent / L-Selectride / tetrahydrofuran / -78 deg C, 1 h; -43 deg C, 12 h
3: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
4: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
5: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
6: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
7: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 7 steps
1: 93 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -78 °C
2: 80 percent / L-Selectride / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -43 deg C, 12 h
3: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
4: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
5: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
6: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
7: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
<1S-<1α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,6,7,8,8a-hexahydro-7-methyl-1-naphthalenol
117065-48-2

<1S-<1α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,6,7,8,8a-hexahydro-7-methyl-1-naphthalenol

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 99 percent / Et3N / DMAP / CH2Cl2 / 68 h / Ambient temperature
2: 92 percent / Bu4NF / tetrahydrofuran / 1.75 h / Ambient temperature
3: 1.) (COCl)2; 2.) Et3N / 1.) DMSO,CH2Cl2, -78 deg C, 20 min; 2.) -78 deg C, 10 min, -78 deg C -> r.t., 30 min
4: 88 percent / 1.3N HCl / tetrahydrofuran / 2 h / Ambient temperature
5: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
Multi-step reaction with 5 steps
1: 99 percent / Et3N, 4-(dimethylamino)pyridine (DMAP) / CH2Cl2 / 68 h / Ambient temperature
2: 92 percent / Bu4N(1+)*F(1-) / tetrahydrofuran / 1.75 h / Ambient temperature
3: 91 percent / (COCl)2, DMSO / CH2Cl2 / 0.33 h / -78 °C
4: 88 percent / 10percent aq. HCl / tetrahydrofuran / 2 h / Ambient temperature
5: 61 percent / Ag2CO3/Celite / toluene / 2 h / 95 °C
View Scheme
(R)-3-<(tert-butyldimethylsilyl)oxy>-6-(dimethoxyphosphinyl)-5-oxohexanoic acid
96555-55-4

(R)-3-<(tert-butyldimethylsilyl)oxy>-6-(dimethoxyphosphinyl)-5-oxohexanoic acid

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 92 percent / diethyl ether / 0.25 h / Ambient temperature
2: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature
3: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C
4: aq. HF / acetonitrile / 0.83 h / Ambient temperature
5: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C
6: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature
View Scheme
Multi-step reaction with 6 steps
2: LiCl/DBU / acetonitrile
3: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C
4: HF / acetonitrile
5: NaBH4 / 0.5 h / -15 °C
6: 70 percent / p-TsOH / benzene
View Scheme
(R)-6-(Dimethoxyphosphinyl)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-oxohexanoic acid, methylester
96555-58-7

(R)-6-(Dimethoxyphosphinyl)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-oxohexanoic acid, methylester

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature
2: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C
3: aq. HF / acetonitrile / 0.83 h / Ambient temperature
4: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C
5: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature
View Scheme
Multi-step reaction with 5 steps
1: LiCl/DBU / acetonitrile
2: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C
3: HF / acetonitrile
4: NaBH4 / 0.5 h / -15 °C
5: 70 percent / p-TsOH / benzene
View Scheme
(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-formyl-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester
96575-19-8

(S)-2-Methyl-butyric acid (1S,7S,8S,8aR)-8-formyl-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature
2: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C
3: aq. HF / acetonitrile / 0.83 h / Ambient temperature
4: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C
5: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature
View Scheme
Multi-step reaction with 5 steps
1: LiCl/DBU / acetonitrile
2: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C
3: HF / acetonitrile
4: NaBH4 / 0.5 h / -15 °C
5: 70 percent / p-TsOH / benzene
View Scheme
(3R,1'R)-methyl 1'-phenylethyl 3-hydroxypentanedioate
96575-20-1

(3R,1'R)-methyl 1'-phenylethyl 3-hydroxypentanedioate

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 1.) N-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, from -78 deg C to RT
2: 84 percent / imidazole / CH2Cl2 / 8 h / Ambient temperature
3: H2 / 10percent Pd/C / diethyl ether / 2 h / 760 Torr / Ambient temperature
4: 92 percent / diethyl ether / 0.25 h / Ambient temperature
5: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature
6: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C
7: aq. HF / acetonitrile / 0.83 h / Ambient temperature
8: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C
9: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature
View Scheme
Multi-step reaction with 9 steps
1: 43 percent / tetrahydrofuran / 0.17 h / -78 °C
2: C3H4N2
3: H2 / Pd-C
5: LiCl/DBU / acetonitrile
6: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C
7: HF / acetonitrile
8: NaBH4 / 0.5 h / -15 °C
9: 70 percent / p-TsOH / benzene
View Scheme
(3R,1'R)-methyl 1'-phenylethyl 3-<(tert-butyldimethylsilyl)oxy>pentanedioate
96555-51-0

(3R,1'R)-methyl 1'-phenylethyl 3-<(tert-butyldimethylsilyl)oxy>pentanedioate

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 99 percent / aq. HF / acetonitrile / 1.25 h / Ambient temperature
2: 1.) N-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, from -78 deg C to RT
3: 84 percent / imidazole / CH2Cl2 / 8 h / Ambient temperature
4: H2 / 10percent Pd/C / diethyl ether / 2 h / 760 Torr / Ambient temperature
5: 92 percent / diethyl ether / 0.25 h / Ambient temperature
6: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature
7: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C
8: aq. HF / acetonitrile / 0.83 h / Ambient temperature
9: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C
10: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature
View Scheme
Multi-step reaction with 10 steps
1: HF / acetonitrile
2: 43 percent / tetrahydrofuran / 0.17 h / -78 °C
3: C3H4N2
4: H2 / Pd-C
6: LiCl/DBU / acetonitrile
7: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C
8: HF / acetonitrile
9: NaBH4 / 0.5 h / -15 °C
10: 70 percent / p-TsOH / benzene
View Scheme
(R)-dimethyl <<4-<<(R)-phenylethoxy>carbonyl>-3-hydroxybutyryl>methyl>phosphonate
96555-53-2

(R)-dimethyl <<4-<<(R)-phenylethoxy>carbonyl>-3-hydroxybutyryl>methyl>phosphonate

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 84 percent / imidazole / CH2Cl2 / 8 h / Ambient temperature
2: H2 / 10percent Pd/C / diethyl ether / 2 h / 760 Torr / Ambient temperature
3: 92 percent / diethyl ether / 0.25 h / Ambient temperature
4: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature
5: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C
6: aq. HF / acetonitrile / 0.83 h / Ambient temperature
7: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C
8: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature
View Scheme
Multi-step reaction with 8 steps
1: C3H4N2
2: H2 / Pd-C
4: LiCl/DBU / acetonitrile
5: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C
6: HF / acetonitrile
7: NaBH4 / 0.5 h / -15 °C
8: 70 percent / p-TsOH / benzene
View Scheme
(R)-dimethyl <<3-<(tert-butyldimethylsilyl)oxy>-4-<<(R)-phenylethoxy>carbonyl>butyryl>methyl>phosphonate
96555-54-3

(R)-dimethyl <<3-<(tert-butyldimethylsilyl)oxy>-4-<<(R)-phenylethoxy>carbonyl>butyryl>methyl>phosphonate

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: H2 / 10percent Pd/C / diethyl ether / 2 h / 760 Torr / Ambient temperature
2: 92 percent / diethyl ether / 0.25 h / Ambient temperature
3: 55 percent / LiCl, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / dimethylsulfoxide / 30 h / Ambient temperature
4: (Ph3P)3RhCl, Et3SiH / benzene / 0.58 h / 70 °C
5: aq. HF / acetonitrile / 0.83 h / Ambient temperature
6: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C
7: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature
View Scheme
Multi-step reaction with 7 steps
1: H2 / Pd-C
3: LiCl/DBU / acetonitrile
4: Et3SiH/(Ph3p)3ClRh / toluene / 65 °C
5: HF / acetonitrile
6: NaBH4 / 0.5 h / -15 °C
7: 70 percent / p-TsOH / benzene
View Scheme
(1S,2S,8S,8aR,5'R,2''S)-methyl 1,2,6,7,8,8a-hexahydro-5'hydroxy-2-methyl-8-<(2-methyl-1-oxobutyl)oxy>-3'-oxo-1-naphthaleneheptanoate
96555-61-2

(1S,2S,8S,8aR,5'R,2''S)-methyl 1,2,6,7,8,8a-hexahydro-5'hydroxy-2-methyl-8-<(2-methyl-1-oxobutyl)oxy>-3'-oxo-1-naphthaleneheptanoate

mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 9.6 mg / NaBH4 / methanol / 0.45 h / -15 - -13 °C
2: 70 percent / p-TsOH*H2O / benzene / 1.08 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: NaBH4 / 0.5 h / -15 °C
2: 70 percent / p-TsOH / benzene
View Scheme
mevastatin
73573-88-3

mevastatin

Conditions
ConditionsYield
85.4%
Product distribution / selectivity;
mevastatin
73573-88-3

mevastatin

<1S-<1α(3R*,5S*),2α,8β,8aα>>-7-(1,2,6,7,8,8a-Hexahydro-8-hydroxy-2-methyl-1-naphthalenyl)-1,3,5-heptanetriol
161466-60-0

<1S-<1α(3R*,5S*),2α,8β,8aα>>-7-(1,2,6,7,8,8a-Hexahydro-8-hydroxy-2-methyl-1-naphthalenyl)-1,3,5-heptanetriol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 9h; Ambient temperature;81%
With lithium aluminium tetrahydride In diethyl ether
mevastatin
73573-88-3

mevastatin

6-desmethylmonacolin J
58889-19-3

6-desmethylmonacolin J

Conditions
ConditionsYield
With lithium hydroxide for 24h; Heating;75%
Multi-step reaction with 2 steps
1: aq. LiOH / 24 h / Heating
2: 30 mg / toluene / 1 h / Heating
View Scheme
mevastatin
73573-88-3

mevastatin

(1S,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-7-methyl-8-<2-((2R,4R)-tetrahydro-4-methoxy-6-oxo-2H-pyran-2-yl)-ethyl>-1-naphthyl (2S)-2-methylbutyrate
84751-53-1

(1S,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-7-methyl-8-<2-((2R,4R)-tetrahydro-4-methoxy-6-oxo-2H-pyran-2-yl)-ethyl>-1-naphthyl (2S)-2-methylbutyrate

Conditions
ConditionsYield
In diethyl ether; water at 0℃;38%
formic acid
64-18-6

formic acid

mevastatin
73573-88-3

mevastatin

(S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-4-chloro-6-formyloxy-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester
153079-18-6

(S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-4-chloro-6-formyloxy-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester

Conditions
ConditionsYield
With tert-butylhypochlorite In dichloromethane at -10℃; Product distribution; Mechanism; reactions 1 or 2 equiv. terc-BuOCl;
With tert-butylhypochlorite In dichloromethane at -10℃;
formic acid
64-18-6

formic acid

mevastatin
73573-88-3

mevastatin

(S)-2-Methyl-butyric acid (1S,4S,5R,6S,7R,8S)-4,5-dichloro-6-formyloxy-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,5,6,7,8-octahydro-naphthalen-1-yl ester

(S)-2-Methyl-butyric acid (1S,4S,5R,6S,7R,8S)-4,5-dichloro-6-formyloxy-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,5,6,7,8-octahydro-naphthalen-1-yl ester

Conditions
ConditionsYield
With tert-butylhypochlorite In dichloromethane at -10℃;
mevastatin
73573-88-3

mevastatin

anhydrocompactin
84173-32-0

anhydrocompactin

Conditions
ConditionsYield
With potassium hydrogensulfate In N,N-dimethyl-formamide for 6h; Heating;2.7 mg
tert-butoxy radical
3141-58-0

tert-butoxy radical

mevastatin
73573-88-3

mevastatin

A

acetone
67-64-1

acetone

B

tert-butyl alcohol
75-65-0

tert-butyl alcohol

Conditions
ConditionsYield
In acetonitrile at 40℃; for 15h; Kinetics; Product distribution;
mevastatin
73573-88-3

mevastatin

(3R,5R)-3,5-Dihydroxy-7-((1S,2S,8S,8aR)-8-hydroxy-2-methyl-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl)-heptanoic acid

(3R,5R)-3,5-Dihydroxy-7-((1S,2S,8S,8aR)-8-hydroxy-2-methyl-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl)-heptanoic acid

Conditions
ConditionsYield
With lithium hydroxide for 24h; Heating;
ethanol
64-17-5

ethanol

mevastatin
73573-88-3

mevastatin

3,5-dihydroxy-7-[2-methyl-8-(2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-heptanoic acid ethyl ester

3,5-dihydroxy-7-[2-methyl-8-(2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-heptanoic acid ethyl ester

Conditions
ConditionsYield
With potassium hydroxide
mevastatin
73573-88-3

mevastatin

(S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-4-chloro-6-formyloxy-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester
153079-18-6

(S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-4-chloro-6-formyloxy-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester

mevastatin
73573-88-3

mevastatin

Acetic acid (1S,7S,8S,8aR)-7-methyl-8-((3R,5S)-3,5,7-triacetoxy-heptyl)-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

Acetic acid (1S,7S,8S,8aR)-7-methyl-8-((3R,5S)-3,5,7-triacetoxy-heptyl)-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: LiAlH4 / diethyl ether
2: pyridine, DMAP
View Scheme
mevastatin
73573-88-3

mevastatin

<4R-<4α(4R*,5R*),6α>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-one
116996-32-8

<4R-<4α(4R*,5R*),6α>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-one

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 79 percent / LDA, Et3N / 0.42 h / -78 °C
10: 1.) m-CPBA, 2.) Bu4NF, AcOH
11: AcOH / methanol / 11 h
12: PPTS / 7.5 h
13: aq. NaIO4 / methanol / 23 h / Ambient temperature
14: PPTS / 2.5 h
View Scheme
Multi-step reaction with 13 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 1.) potassium bis(trimethylsilyl)amide, 2-(phenylsulfonyl)-3-(p-nitrophenyl)oxaziridine, 2.) Bu4NF / 1.) THF, toluene, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, 30 min
10: AcOH / methanol / 11 h
11: PPTS / 7.5 h
12: aq. NaIO4 / methanol / 23 h / Ambient temperature
13: PPTS / 2.5 h
View Scheme
mevastatin
73573-88-3

mevastatin

<1S-<1α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,6,7,8,8a-hexahydro-7-methyl-1-naphthalenol
117065-48-2

<1S-<1α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,6,7,8,8a-hexahydro-7-methyl-1-naphthalenol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
View Scheme
mevastatin
73573-88-3

mevastatin

(4R,5R)-5-[(3R,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-heptyl]-4-methyl-cyclohex-2-enone

(4R,5R)-5-[(3R,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-heptyl]-4-methyl-cyclohex-2-enone

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 79 percent / LDA, Et3N / 0.42 h / -78 °C
10: 1.) m-CPBA, 2.) Bu4NF, AcOH
11: AcOH / methanol / 11 h
12: PPTS / 7.5 h
13: aq. NaIO4 / methanol / 23 h / Ambient temperature
View Scheme
Multi-step reaction with 12 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 1.) potassium bis(trimethylsilyl)amide, 2-(phenylsulfonyl)-3-(p-nitrophenyl)oxaziridine, 2.) Bu4NF / 1.) THF, toluene, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, 30 min
10: AcOH / methanol / 11 h
11: PPTS / 7.5 h
12: aq. NaIO4 / methanol / 23 h / Ambient temperature
View Scheme
mevastatin
73573-88-3

mevastatin

<1S-<1α(3R*,5S*),2α,8β,8aα>>-1<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-7-(1,2,6,7,8,8a-hexahydro-8-hydroxy-2-methyl-1-naphthalenyl)-3,5-heptanediol
126060-27-3

<1S-<1α(3R*,5S*),2α,8β,8aα>>-1<<(1,1-Dimethylethyl)diphenylsilyl>oxy>-7-(1,2,6,7,8,8a-hexahydro-8-hydroxy-2-methyl-1-naphthalenyl)-3,5-heptanediol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
View Scheme
mevastatin
73573-88-3

mevastatin

<1aR-<1aα,4β,4aα,5α(4R*,6S*),6α>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1a,2,4,4a,5,6-hexahydro-6-methyl-3H-naphth<1,8a-b>oxiren-4-ol
161466-61-1

<1aR-<1aα,4β,4aα,5α(4R*,6S*),6α>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1a,2,4,4a,5,6-hexahydro-6-methyl-3H-naphth<1,8a-b>oxiren-4-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
View Scheme
mevastatin
73573-88-3

mevastatin

(4R,7S,8S,8aR)-8-[(3R,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-heptyl]-2,4,4a-trihydroxy-7-methyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-one

(4R,7S,8S,8aR)-8-[(3R,5S)-7-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-heptyl]-2,4,4a-trihydroxy-7-methyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-one

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 79 percent / LDA, Et3N / 0.42 h / -78 °C
10: 1.) m-CPBA, 2.) Bu4NF, AcOH
11: AcOH / methanol / 11 h
View Scheme
Multi-step reaction with 10 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 1.) potassium bis(trimethylsilyl)amide, 2-(phenylsulfonyl)-3-(p-nitrophenyl)oxaziridine, 2.) Bu4NF / 1.) THF, toluene, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, 30 min
10: AcOH / methanol / 11 h
View Scheme
mevastatin
73573-88-3

mevastatin

<4R-<4α,7β,8β(4R*,6S*),8aβ>>-4-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-3,4,4a,7,8,8a-hexahydro-2,4,4a-trihydroxy-7-methyl-1(2H)naphthalenone

<4R-<4α,7β,8β(4R*,6S*),8aβ>>-4-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-3,4,4a,7,8,8a-hexahydro-2,4,4a-trihydroxy-7-methyl-1(2H)naphthalenone

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 79 percent / LDA, Et3N / 0.42 h / -78 °C
10: 1.) m-CPBA, 2.) Bu4NF, AcOH
11: AcOH / methanol / 11 h
12: PPTS / 7.5 h
View Scheme
Multi-step reaction with 11 steps
1: 81 percent / LiAlH4 / tetrahydrofuran / 9 h / Ambient temperature
2: 92 percent / imidazole / dimethylformamide / 1 h
3: 89 percent / PPTS / CH2Cl2 / 0.17 h / 0 °C
4: 89 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 2 h / Ambient temperature
5: 1.) Li, CuCN / 1.) THF, 2.) THF, 4 h
6: 95 percent / NaHCO3, t-BuOOH, VO(acac)2 / benzene / 6 h / Ambient temperature
7: 84 percent / Et3N, DMAP / CH2Cl2 / 0.17 h / 0 °C
8: 98 percent / Pr4NRuO4, 4 Angstroem molecular sieves, 4-methylmorpholine N-oxide / CH2Cl2 / 6 h
9: 1.) potassium bis(trimethylsilyl)amide, 2-(phenylsulfonyl)-3-(p-nitrophenyl)oxaziridine, 2.) Bu4NF / 1.) THF, toluene, -78 deg C, 30 min; -78 deg C, 30 min, 2.) THF, 30 min
10: AcOH / methanol / 11 h
11: PPTS / 7.5 h
View Scheme

73573-88-3Relevant articles and documents

FED BATCH SOLID STATE FERMENTATION FOR THE PRODUCTION OF HMG-COA REDUCTASE INHIBITORS

-

Page 12 - 13, (2008/06/13)

The present invention provides a novel method for producing compound of formula (I), its acid form or any salt form, where R1 is H or CH3, by solid state fermentation using fed-batch technique by culturing microorganisms capable of producing the compound of formula (I).

Method for producing pharmaceutical dosage forms

-

, (2008/06/13)

The invention relates to a method for producing a granulate while using spray-dried D-mannitol and to the production of pharmaceutical dosage forms comprised of granulates of this type. The invention additionally relates to granulates obtained by using this method and to pharmaceutical dosage forms, which contain statins, especially cerivastatin, and which can be produced from said granulates.

Antihypercholesterolemic compounds and synthesis thereof

-

, (2008/06/13)

A method of preparing compactin and mevinolin, ketoacid, enone, and glutarate analogs thereof, and related compounds. The compounds are prepared in substantially enantiomerically pure form using a structurally convergent synthesis. Total syntheses of (+)-compactin, (+)-mevinolin and related compounds are provided. Novel compounds are identified, several of which show significant anti-hypercholesterolemic activity.

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