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124655-09-0

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  • (4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester Manufacturer/High quality/Best price/In stock

    Cas No: 124655-09-0

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  • High quality (4R-Cis)-6-Hydroxymethyl-2,2-Dimethyl-1,3-Dioxane-4-Acetic Acid 1,1-Dimethylethyl Ester supplier in China

    Cas No: 124655-09-0

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  • (4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester, Rosuvastatin Intermediate D6, 124655-09-0

    Cas No: 124655-09-0

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  • Factory Supply .sc.d.sc.-erythro-hexanoic acid 2,4-dideoxy-3,5-O-(1-methylethylidene)-1,1-dimethylethylester; tert-butyl 2-[(4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetate

    Cas No: 124655-09-0

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  • High Quality 99% 124655-09-0 T-butyl-(3R,5S)-6-hydroxy 3,5-O-isopropylidene 3,5-dihydroxyhexanoate Manufacturer

    Cas No: 124655-09-0

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124655-09-0 Usage

Description

(4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester is a colorless to light yellow liquid that serves as a valuable synthetic intermediate in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
(4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester is used as a synthetic intermediate for the preparation of Rosuvastatin (R700500) and its derivatives. (4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester plays a crucial role in the development of statin drugs, which are widely used for the treatment of high cholesterol and cardiovascular diseases. Its unique structure allows for the synthesis of various pharmaceutical compounds, making it an essential component in the production process.

Check Digit Verification of cas no

The CAS Registry Mumber 124655-09-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,4,6,5 and 5 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 124655-09:
(8*1)+(7*2)+(6*4)+(5*6)+(4*5)+(3*5)+(2*0)+(1*9)=120
120 % 10 = 0
So 124655-09-0 is a valid CAS Registry Number.
InChI:InChI=1/C13H24O5/c1-12(2,3)18-11(15)7-9-6-10(8-14)17-13(4,5)16-9/h9-10,14H,6-8H2,1-5H3/t9-,10+/m1/s1

124655-09-0 Well-known Company Product Price

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  • TCI America

  • (B4214)  tert-Butyl (4R,6S)-6-(Hydroxymethyl)-2,2-dimethyl-1,3-dioxane-4-acetate  >98.0%(GC)

  • 124655-09-0

  • 5g

  • 990.00CNY

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  • TCI America

  • (B4214)  tert-Butyl (4R,6S)-6-(Hydroxymethyl)-2,2-dimethyl-1,3-dioxane-4-acetate  >98.0%(GC)

  • 124655-09-0

  • 25g

  • 3,750.00CNY

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124655-09-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name (4R-Cis)-6-Hydroxymethyl-2,2-Dimethyl-1,3-Dioxane-4-Acetic Acid 1,1-Dimethylethyl Ester

1.2 Other means of identification

Product number -
Other names (4R,6S)-6-(Hydroxymethyl)-2,2-dimethyl-1,3-dioxane-4-acetic Acid tert-Butyl Ester

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:124655-09-0 SDS

124655-09-0Synthetic route

tert-butyl 2-((4R,6S)-6-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetate
151140-38-4

tert-butyl 2-((4R,6S)-6-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate at 31 - 33℃; under 7600 Torr; for 5h;100%
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 750.075 - 1500.15 Torr; Autoclave;94%
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 5h; Concentration;94%
With H2; palladium-carbon In ethyl acetate
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 25 - 30℃; under 7500.75 Torr; for 5h; Autoclave;
(4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester
154026-95-6

(4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
With potassium carbonate In methanol; water98%
With methanol; potassium carbonate for 0.5h;98%
With methanol; potassium carbonate at 20℃;92%
tert-butyl (3R,5S)-6-(4-methylbenzyloxy)-3,5-O-isopropylidene-3,5-dihydroxyhexanoate

tert-butyl (3R,5S)-6-(4-methylbenzyloxy)-3,5-O-isopropylidene-3,5-dihydroxyhexanoate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate at 32℃; under 15201 Torr; for 16h;90%
tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate
124752-23-4

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0℃; for 2h;83%
With sodium tetrahydroborate In methanol at 0℃;
C18H32O6
1067638-10-1

C18H32O6

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 20℃; for 15h;81%
tert-butyl 2-((4R,6S)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate
124655-08-9

tert-butyl 2-((4R,6S)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 3h;80%
tert-butyl 2-((4R, 6S)-2,2-dimethyl-6-((E)-styryl)-1,3-dioxan-4-yl)acetate
143840-61-3

tert-butyl 2-((4R, 6S)-2,2-dimethyl-6-((E)-styryl)-1,3-dioxan-4-yl)acetate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
With sodium tetrahydroborate; ozone 1.) methanol; Yield given. Multistep reaction;
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature
2: 83 percent / sodium borohydride / methanol / 2 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature
2: NaBH4 / methanol / 0 °C
View Scheme
isopropyl (2S,3R,4S,6R)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-dihydroxyheptanoate
147489-00-7

isopropyl (2S,3R,4S,6R)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-dihydroxyheptanoate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 99 percent / p-toluenesulfonic acid / 2 h / Ambient temperature
2: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature
3: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature
4: 83 percent / sodium borohydride / methanol / 2 h / 0 °C
View Scheme
Multi-step reaction with 4 steps
1: 98 percent / p-TsOH / 2 h / Ambient temperature
2: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature
3: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature
4: NaBH4 / methanol / 0 °C
View Scheme
isopropyl (2S,3R,4S,6R)-7-t-butpxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-isopropylidenedioxyheptanoate
147489-01-8

isopropyl (2S,3R,4S,6R)-7-t-butpxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-isopropylidenedioxyheptanoate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature
2: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature
3: 83 percent / sodium borohydride / methanol / 2 h / 0 °C
View Scheme
Multi-step reaction with 3 steps
1: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature
2: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature
3: NaBH4 / methanol / 0 °C
View Scheme
isopropyl (2S,3S,6R)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-6-hydroxy-4-oxoheptanoate
147488-99-1

isopropyl (2S,3S,6R)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-6-hydroxy-4-oxoheptanoate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1.) diethyl(methoxy)borane, 2.) sodium borohydride / 1.) THF, methanol, RT, 15 min, 2.) THF, methanol, a) -78 deg C, 4 h, b) from -78 deg C to RT, 8 h
2: 99 percent / p-toluenesulfonic acid / 2 h / Ambient temperature
3: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature
4: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature
5: 83 percent / sodium borohydride / methanol / 2 h / 0 °C
View Scheme
Multi-step reaction with 5 steps
1: 76 percent / Et2BOMe, NaBH4 / tetrahydrofuran; methanol / -78 deg C to RT, 12 h
2: 98 percent / p-TsOH / 2 h / Ambient temperature
3: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature
4: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature
5: NaBH4 / methanol / 0 °C
View Scheme
isopropyl (2S,3S)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-dioxoheptanoate
147488-98-0

isopropyl (2S,3S)-7-t-butoxycarbonyl-2,3-bis(t-butyldimethylsilyloxy)-4,6-dioxoheptanoate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 60 percent / DIBAL / tetrahydrofuran; hexane / 4 h / -78 °C
2: 1.) diethyl(methoxy)borane, 2.) sodium borohydride / 1.) THF, methanol, RT, 15 min, 2.) THF, methanol, a) -78 deg C, 4 h, b) from -78 deg C to RT, 8 h
3: 99 percent / p-toluenesulfonic acid / 2 h / Ambient temperature
4: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature
5: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature
6: 83 percent / sodium borohydride / methanol / 2 h / 0 °C
View Scheme
Multi-step reaction with 6 steps
1: 60 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 4 h / -78 °C
2: 76 percent / Et2BOMe, NaBH4 / tetrahydrofuran; methanol / -78 deg C to RT, 12 h
3: 98 percent / p-TsOH / 2 h / Ambient temperature
4: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature
5: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature
6: NaBH4 / methanol / 0 °C
View Scheme
tert-butyl acetoacetate
1694-31-1

tert-butyl acetoacetate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 74 percent / NaH, n-BuLi / 20 h / -78 °C
2: 60 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 4 h / -78 °C
3: 76 percent / Et2BOMe, NaBH4 / tetrahydrofuran; methanol / -78 deg C to RT, 12 h
4: 98 percent / p-TsOH / 2 h / Ambient temperature
5: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature
6: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature
7: NaBH4 / methanol / 0 °C
View Scheme
(3R,5S)-3,5-Dihydroxy-5-((2S,3S)-3-trimethylsilanyl-oxiranyl)-pentanoic acid tert-butyl ester
143827-05-8

(3R,5S)-3,5-Dihydroxy-5-((2S,3S)-3-trimethylsilanyl-oxiranyl)-pentanoic acid tert-butyl ester

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 81 percent / H(1+)
2: 1.) Bu3SnLi / 2.) Pd(PPh3)4
3: 1.) O3, 2.) NaBH4 / 1.) methanol
View Scheme
Multi-step reaction with 3 steps
1: 81 percent / H(1+)
2: 90 percent
3: 1.) O3, 2.) NaBH4 / 1.) methanol
View Scheme
(S)-5-Hydroxy-3-oxo-5-((2S,3S)-3-trimethylsilanyl-oxiranyl)-pentanoic acid tert-butyl ester
143840-67-9

(S)-5-Hydroxy-3-oxo-5-((2S,3S)-3-trimethylsilanyl-oxiranyl)-pentanoic acid tert-butyl ester

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 60 percent / Et2BOMe, NaBH4
2: 81 percent / H(1+)
3: 1.) Bu3SnLi / 2.) Pd(PPh3)4
4: 1.) O3, 2.) NaBH4 / 1.) methanol
View Scheme
Multi-step reaction with 4 steps
1: 60 percent / Et2BOMe, NaBH4
2: 81 percent / H(1+)
3: 90 percent
4: 1.) O3, 2.) NaBH4 / 1.) methanol
View Scheme
[(4R,6S)-2,2-Dimethyl-6-((2S,3S)-3-trimethylsilanyl-oxiranyl)-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester
143800-10-6

[(4R,6S)-2,2-Dimethyl-6-((2S,3S)-3-trimethylsilanyl-oxiranyl)-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) Bu3SnLi / 2.) Pd(PPh3)4
2: 1.) O3, 2.) NaBH4 / 1.) methanol
View Scheme
Multi-step reaction with 2 steps
1: 90 percent
2: 1.) O3, 2.) NaBH4 / 1.) methanol
View Scheme
acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 100 percent / LDA / tetrahydrofuran / 1.75 h / -70 - -15 °C
2: 1). Et3B; 2.) NaBH4, MeOH / 1.) THF, 23 deg C, 15 min; 2.) -70 deg C
3: 70 percent / p-toluenesulfonic acid / acetone / 2 h / 23 °C
4: 80 percent / Bu4NF / tetrahydrofuran / 3 h / 0 °C
View Scheme
Multi-step reaction with 5 steps
1.1: lithium diisopropyl amide / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
1.2: 2 h / 20 °C / Inert atmosphere
2.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
2.2: 6 h / 20 °C / Inert atmosphere
3.1: methanol; diethyl methoxy borane; sodium tetrahydroborate / tetrahydrofuran / 2.5 h / -80 - -70 °C / Inert atmosphere
4.1: methanesulfonic acid / 20 °C
5.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 750.08 - 1500.15 Torr / Autoclave
View Scheme
Multi-step reaction with 3 steps
1.1: (S)-5-benzyl 2,2,3-trimethyl-4-thione / ethanol / 0.5 h / 0 °C
1.2: 3 h / 0 - 30 °C
2.1: camphor-10-sulfonic acid / ethyl acetate / 4 h / 20 °C
3.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 5 h / 20 °C
View Scheme
(3R,5S)-tert-butyl 6-(tert-butyldiphenylsilyloxy)-3,5-dihydroxyhexanoate
124655-07-8

(3R,5S)-tert-butyl 6-(tert-butyldiphenylsilyloxy)-3,5-dihydroxyhexanoate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / p-toluenesulfonic acid / acetone / 2 h / 23 °C
2: 80 percent / Bu4NF / tetrahydrofuran / 3 h / 0 °C
View Scheme
(5S)-6-(tert-butyl-diphenylsilanyloxy)-5-hydroxy-3-oxohexanoic acid tert-butyl ester
124655-06-7

(5S)-6-(tert-butyl-diphenylsilanyloxy)-5-hydroxy-3-oxohexanoic acid tert-butyl ester

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1). Et3B; 2.) NaBH4, MeOH / 1.) THF, 23 deg C, 15 min; 2.) -70 deg C
2: 70 percent / p-toluenesulfonic acid / acetone / 2 h / 23 °C
3: 80 percent / Bu4NF / tetrahydrofuran / 3 h / 0 °C
View Scheme
1-methyl 6-tert.-butyl (2S,4R)-2,4-O-isopropylidene-2,4-dihydroxyadipate
140387-94-6

1-methyl 6-tert.-butyl (2S,4R)-2,4-O-isopropylidene-2,4-dihydroxyadipate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
With hydrogenchloride; sodium borohydrid; ammonium chloride In tetrahydrofuran; methanol
With hydrogenchloride; sodium borohydrid; ammonium chloride In methanol
C13H25ClO4Si

C13H25ClO4Si

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hydrogenchloride / water / 1 h / 0 °C
2.1: sodium tetrahydroborate / water / 14 h / 0 °C
3.1: acetone / 0.25 h / 25 °C
3.2: 6 h / 48 - 50 °C
4.1: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
5.1: potassium carbonate; methanol / 0.5 h
View Scheme
Multi-step reaction with 5 steps
1.1: hydrogenchloride / water / 1 h / 0 °C
2.1: diethyl methoxy borane / tetrahydrofuran; methanol / 1 h / 25 °C / Inert atmosphere
2.2: 4 h / -78 °C / Inert atmosphere
3.1: acetone / 0.25 h
3.2: 6 h / 48 - 50 °C
4.1: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
5.1: potassium carbonate; methanol / 0.5 h
View Scheme
Multi-step reaction with 5 steps
1.1: hydrogenchloride / water / 1 h / 0 °C
2.1: sodium tetrahydroborate; sodium dodecyl-sulfate / water / 14 h / 0 °C
3.1: acetone / 0.25 h
3.2: 6 h / 48 - 50 °C
4.1: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
5.1: potassium carbonate; methanol / 0.5 h
View Scheme
Multi-step reaction with 5 steps
1: hydrogenchloride / water / 1 h / 0 °C
2: sodium tetrahydroborate / water / 14 h / 0 °C
3: (R)-10-camphorsulfonic acid / dichloromethane / 3 h / 40 °C
4: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
5: potassium carbonate; methanol / 0.5 h
View Scheme
(5S)-tert-butyl 6-chloro-3,5-dihydroxyhexanoate
406680-96-4

(5S)-tert-butyl 6-chloro-3,5-dihydroxyhexanoate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: acetone / 0.25 h / 25 °C
1.2: 6 h / 48 - 50 °C
2.1: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
3.1: potassium carbonate; methanol / 0.5 h
View Scheme
Multi-step reaction with 3 steps
1: (R)-10-camphorsulfonic acid / dichloromethane / 3 h / 40 °C
2: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
3: potassium carbonate; methanol / 0.5 h
View Scheme
tert-butyl 2-((6S)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

tert-butyl 2-((6S)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 85 °C
2: potassium carbonate; methanol / 0.5 h
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride / water; dichloromethane / 24 h / 20 °C
2: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
3: potassium carbonate; methanol / 0.5 h
View Scheme
Tert-butyl (5S)-6-chloro-5-hydroxy-3-oxohexanoate
154026-92-3

Tert-butyl (5S)-6-chloro-5-hydroxy-3-oxohexanoate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium tetrahydroborate / water / 14 h / 0 °C
2.1: acetone / 0.25 h / 25 °C
2.2: 6 h / 48 - 50 °C
3.1: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
4.1: potassium carbonate; methanol / 0.5 h
View Scheme
Multi-step reaction with 4 steps
1.1: diethyl methoxy borane / tetrahydrofuran; methanol / 1 h / 25 °C / Inert atmosphere
1.2: 4 h / -78 °C / Inert atmosphere
2.1: acetone / 0.25 h
2.2: 6 h / 48 - 50 °C
3.1: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
4.1: potassium carbonate; methanol / 0.5 h
View Scheme
Multi-step reaction with 4 steps
1.1: sodium tetrahydroborate; sodium dodecyl-sulfate / water / 14 h / 0 °C
2.1: acetone / 0.25 h
2.2: 6 h / 48 - 50 °C
3.1: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
4.1: potassium carbonate; methanol / 0.5 h
View Scheme
1,1-dimethylethyl (3R,5S)-6-chloro-3,5-dihydroxy-4-hexanoate
154026-93-4

1,1-dimethylethyl (3R,5S)-6-chloro-3,5-dihydroxy-4-hexanoate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: acetone / 0.25 h
1.2: 6 h / 48 - 50 °C
2.1: 1-methyl-pyrrolidin-2-one / 24 h / 25 - 95 °C
3.1: potassium carbonate; methanol / 0.5 h
View Scheme
Multi-step reaction with 3 steps
1: (1S)-10-camphorsulfonic acid / acetone / 6 h / 48 - 50 °C
2: 1-methyl-pyrrolidin-2-one / 24 h / 95 °C
3: methanol; potassium carbonate / 20 °C
View Scheme
tert-butyl 2-((6S)-6-(acetoxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

tert-butyl 2-((6S)-6-(acetoxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water; dichloromethane / 48 h / 25 °C
2: potassium carbonate; methanol / 0.5 h
View Scheme
(4R-cis)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid,1,1-dimethylethyl ester
154026-94-5

(4R-cis)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid,1,1-dimethylethyl ester

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-methyl-pyrrolidin-2-one / 24 h / 95 °C
2: methanol; potassium carbonate / 20 °C
View Scheme
tert-butyl (S)-4-(propylene oxide-2-yl)-3-oxobutanoate
623566-51-8

tert-butyl (S)-4-(propylene oxide-2-yl)-3-oxobutanoate

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
1.2: 6 h / 20 °C / Inert atmosphere
2.1: methanol; diethyl methoxy borane; sodium tetrahydroborate / tetrahydrofuran / 2.5 h / -80 - -70 °C / Inert atmosphere
3.1: methanesulfonic acid / 20 °C
4.1: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C / 750.08 - 1500.15 Torr / Autoclave
View Scheme
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetic acid
154877-92-6

2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetic acid

Conditions
ConditionsYield
Stage #1: 1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate With water; sodium hydroxide In methanol at 40 - 50℃;
Stage #2: With hydrogenchloride In water at 15 - 20℃; pH=4 - 4.2;
100%
With sodium hydroxide In tetrahydrofuran Reflux;
With sodium hydroxide In tetrahydrofuran Reflux;
1H-imidazole
288-32-4

1H-imidazole

ethyl acetate dichloromethane

ethyl acetate dichloromethane

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

(3R,5S)-6-iodo-3,5-O-isopropylidene-3,5-dihydroxyhexanoic acid tert-butyl ester
134742-42-0

(3R,5S)-6-iodo-3,5-O-isopropylidene-3,5-dihydroxyhexanoic acid tert-butyl ester

Conditions
ConditionsYield
With iodine; triphenylphosphine In benzene99%
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

C13H24O5

C13H24O5

Conditions
ConditionsYield
With toluene-4-sulfonic acid In acetone at 50℃;99%
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate
124752-23-4

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

Conditions
ConditionsYield
Swern oxidation; (further oxidizing agents);97%
Stage #1: 1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate With dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine In dichloromethane at -5 - 0℃; for 0.5h;
Stage #2: With pyridine; sulfur trioxide pyridine complex; dimethyl sulfoxide In dichloromethane at -5 - 20℃; for 1.16667h;
93%
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide In dichloromethane; water at 5 - 10℃; for 0.166667h; Temperature; Flow reactor;93.5%
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

(3R,5S)-6-<(methylsulfonyl)oxy>-3,5-O-isopropylidene-3,5-dihydroxyhexanoic acid tert-butyl ester
135054-68-1

(3R,5S)-6-<(methylsulfonyl)oxy>-3,5-O-isopropylidene-3,5-dihydroxyhexanoic acid tert-butyl ester

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 0.5h;90%
With pyridine In dichloromethane; toluene
With triethylamine In dichloromethane100 g
C20H19FN2O3
906645-38-3

C20H19FN2O3

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

C33H41FN2O7
906645-40-7

C33H41FN2O7

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at -5 - 20℃; Mitsunobu reaction;88%
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

benzoyl chloride
98-88-4

benzoyl chloride

((4S,6R)-6-(2-tert-butoxy-2-oxoethyl)-2,2-dimethyl-1,3-dioxan-4-yl)methyl benzoate
131666-50-7

((4S,6R)-6-(2-tert-butoxy-2-oxoethyl)-2,2-dimethyl-1,3-dioxan-4-yl)methyl benzoate

Conditions
ConditionsYield
Stage #1: 1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate With pyridine In dichloromethane at 20℃; for 0.5h;
Stage #2: benzoyl chloride In dichloromethane at 20℃; for 1h;
88%
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

acetyl chloride
75-36-5

acetyl chloride

(4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester
154026-95-6

(4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: 1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate With pyridine In dichloromethane at 20℃; for 0.5h;
Stage #2: acetyl chloride In dichloromethane at 20℃; for 1h;
86%
With pyridine In dichloromethane at 20℃; for 0.5h;15.9 g
2-methyl-2-phenylpropionic acid
826-55-1

2-methyl-2-phenylpropionic acid

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

C22H34O5

C22H34O5

Conditions
ConditionsYield
With 2,4,6-trimethyl-pyridine; tetrabutylammonium perchlorate; silver perchlorate In dichloromethane at 20℃; for 3h; Electrolysis; Molecular sieve;52%
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

C17H28O6
707542-98-1

C17H28O6

Conditions
ConditionsYield
With manganese(IV) oxide In toluene for 17h; Heating / reflux;41%
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

C40H44F2N2O5

C40H44F2N2O5

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 46 percent / n-BuLi / 2 h / -78 - 25 °C
View Scheme
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

(6-{2-[3-(4-fluorophenyl)-1-isopropyl-5-(4-methoxybenzylcarbamoyl)-4-phenyl-1H-pyrrol-2-yl]vinyl}-2,2-dimethyl-[1,3]dioxan-4-yl)acetic acid tert-butyl ester
855249-03-5

(6-{2-[3-(4-fluorophenyl)-1-isopropyl-5-(4-methoxybenzylcarbamoyl)-4-phenyl-1H-pyrrol-2-yl]vinyl}-2,2-dimethyl-[1,3]dioxan-4-yl)acetic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 percent / NaHMDS / tetrahydrofuran / 2 h / -78 - 25 °C
View Scheme
1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

C42H51FN2O6

C42H51FN2O6

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 75 percent / NaHMDS / tetrahydrofuran / 2 h / -78 - 25 °C
2: hydrogen / Pd/C / methanol / 3 h / 25 °C / 2585.81 Torr
View Scheme

124655-09-0Relevant articles and documents

STEREOSELECTIVE REDUCTION OF β,δ-DIKETO ESTERS DERIVED FROM TARTARIC ACID. A FACILE ROUTE TO OPTICALLY ACTIVE 6-OXO-3,5-syn-ISOPROPYLIDENEDIOXYHEXANOATE, A VERSATILE SYNTHETIC INTERMEDIATE OF ARTIFICIAL HMG Co-A REDUCTASE INHIBITORS.

Minami, Tatsuya,Takahashi, Kyoko,Hiyama, Tamejiro

, p. 513 - 516 (1993)

Reduction of β,δ-diketo esters derived from tartaric acid with HAl(i-Bu)2 gave stereoselectively β-hydroxy-δ-keto esters which were reduced with NaBH4 and Et2BOMe to β,δ-syn-dihydroxy esters.This strategy was successfully applied to the synthesis of t-butyl (3R,5S)-6-oxo-3,5-isopropylidenedioxyhexanoate starting from D-tartrate.

Preparation method of rosuvastatin calcium intermediate

-

Paragraph 0050-0060, (2021/07/08)

The invention belongs to the technical field of medicinal chemistry and relates to the technical field of drug synthesis, particularly to a preparation method of a high-purity rosuvastatin calcium intermediate. The preparation method of the high-purity rosuvastatin calcium intermediate comprises controlling reaction PH and temperature and applied amount of sodium hypochlorite to control the content of impurities in the high-purity rosuvastatin calcium intermediate shown as the formula I', thereby improving the yield and purity of finished products. The content of impurity compound I' in the high-purity rosuvastatin calcium intermediate prepared through the method is lower than 0.05%. The preparation method of the high-purity rosuvastatin calcium intermediate is highly significant to quality improvement of industrialized production products of the high-purity rosuvastatin calcium intermediate, and further achieves certain assisting and supporting effects on quality improvement as well as registration and declaration of rosuvastatin calcium drugs.

Efficient and Practical Deacylation Reaction System in a Continuous Packed-Bed Reactor

Yasukouchi, Hiroaki,Machida, Koji,Nishiyama, Akira,Mitsuda, Masaru

supporting information, p. 654 - 659 (2019/04/01)

The ester deacylation reaction is widely applied in organic synthesis for preparing desired hydroxy compounds, as the acyl group is often used for protecting the hydroxyl group. This reaction is usually performed by acid, base, or enzyme catalysts, which have to be removed by complicated workups such as extraction or filtration in batch mode. Therefore, a simple deacylation process is desirable to improve productivity, especially at the industrial scale. In this work, we established an efficient and practical packed-bed reactor system for undertaking the deacylation reaction using an anion-exchange resin that provides a simple process compared with batch processing. We also demonstrated that this technique is applicable to the preparation of a wide variety of desired pharmaceutical intermediates containing hydroxy groups in good to excellent yields.

Preparation method of rosuvastatin calcium medicine intermediate

-

Paragraph 0029; 0042; 0045; 0050; 0051; 0056, (2018/11/03)

The invention belongs to the technical field of medicine chemicals, and particularly relates to a preparation method of a rosuvastatin calcium medicine intermediate. The preparation method comprises the following steps of using monochloroacetaldehyde as the raw material; substituting, condensing, and chirally catalyzing, so as to prepare a compound V; protecting by 2,2-dimethoxypropane, and debenzylating, so as to obtain a target compound I. The preparation method has the advantages that the raw materials are easy to obtain; (S)-5-benzyl-2,2,3-trimethyl-4-thioketone is used as a catalyst for stereo selective reduction, the reaction conditions are mild, the yield rate is higher, and the industrialization production of the component I is easy.

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