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59865-23-5

59865-23-5

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59865-23-5 Usage

Uses

4-(2E)-2-Buten-1-yl-2,4,5-trideoxy-2-(methylamino)-L-xylonic Acid is used in the preparation of chiral catalysts for use in organic synthesis.

Check Digit Verification of cas no

The CAS Registry Mumber 59865-23-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,9,8,6 and 5 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 59865-23:
(7*5)+(6*9)+(5*8)+(4*6)+(3*5)+(2*2)+(1*3)=175
175 % 10 = 5
So 59865-23-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H19NO3/c1-4-5-6-7(2)9(12)8(11-3)10(13)14/h4-5,7-9,11-12H,6H2,1-3H3,(H,13,14)/b5-4+/t7-,8+,9-/m1/s1

59865-23-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name (2S,3R,4R)-3-hydroxy-4-methyl-2-(methylamino)oct-6-enoic acid

1.2 Other means of identification

Product number -
Other names -

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:59865-23-5 SDS

59865-23-5Synthetic route

(4S,5R)-3-N-methyl-5-<<(1R,3E)-1-methyl-3-penten>-1-yl>oxazolidin-2-one-4-carboxylic acid
81135-41-3

(4S,5R)-3-N-methyl-5-<<(1R,3E)-1-methyl-3-penten>-1-yl>oxazolidin-2-one-4-carboxylic acid

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
With potassium hydroxide for 5h; Heating;100%
With potassium hydroxide at 80℃; for 3h; 2) pH=5;94%
Multi-step reaction with 2 steps
1: 70 mg / diethyl ether
2: 80 percent / aq. KOH / 10 h / 80 - 95 °C
View Scheme
ethyl (4S,5R)-3-methyl-5-<(1R,3E)-1-methyl-3-pentenyl>-2-oxo-4-oxazolidinecarboxylate
81135-56-0

ethyl (4S,5R)-3-methyl-5-<(1R,3E)-1-methyl-3-pentenyl>-2-oxo-4-oxazolidinecarboxylate

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
With potassium hydroxide at 80℃; for 3h;90%
Multi-step reaction with 2 steps
1: 90 percent / 0.1 N KOH / dioxane / 1 h / Ambient temperature
2: 94 percent / 2 N KOH / 3 h / 80 °C / 2) pH=5
View Scheme
(4S,5R)-4-methoxycarbonyl-2-N-methyl-5-<(1-2,2-dimethyl-2-oxazolidinone" src="//file1.lookchem.com/cas/reactions/2021/05/29/4692981.png_ms" />
104324-29-0

(4S,5R)-4-methoxycarbonyl-2-N-methyl-5-<(1"R,3"E)-1"-methylpent-3"-enyl>-2,2-dimethyl-2-oxazolidinone

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
With potassium hydroxide In water at 75 - 80℃;82%
With potassium hydroxide at 80 - 95℃; for 10h;80%
With potassium hydroxide In water at 80℃; for 3h;76%
With potassium hydroxide Heating;
(2S,3R,4R)-2-(N-(9-phenylfluoren-9-yl)-N-methylamino)-3-hydroxy-4-methyl-6-octynoic acid
126576-06-5

(2S,3R,4R)-2-(N-(9-phenylfluoren-9-yl)-N-methylamino)-3-hydroxy-4-methyl-6-octynoic acid

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
With ammonia; lithium for 0.0333333h; Heating;76%
(2S,3R,4R)-3-hydroxy-4-methyl-2-(methylamino)-6-octynoic acid
124562-10-3

(2S,3R,4R)-3-hydroxy-4-methyl-2-(methylamino)-6-octynoic acid

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
With ammonia; lithium at -20℃; for 0.0833333h;70%
ethyl(2S,3R,4R,6E)-2-(N-formyl-N-methylamino)-3-hydroxy-4-methyloct-6-enoate
127605-68-9

ethyl(2S,3R,4R,6E)-2-(N-formyl-N-methylamino)-3-hydroxy-4-methyloct-6-enoate

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
With potassium hydroxide at 80℃;70%
(3aR,3bS,7R,7aR,8aR)-2,2,7-Trimethyl-hexahydro-[1,3]dioxolo[4,5]furo[3,2-b]pyran-5-one
128254-61-5

(3aR,3bS,7R,7aR,8aR)-2,2,7-Trimethyl-hexahydro-[1,3]dioxolo[4,5]furo[3,2-b]pyran-5-one

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multistep reaction;
Multi-step reaction with 8 steps
1: 1) disiobutylaluminium hydride / 1) CH2Cl2, -78 degC; 2) CH2Cl2
2: 1) pyridinium dichromate, Ac2O; 2) NaBH4 / 1) CH2Cl2; 2) MeOH
3: 1) (CF3SO2)2O, pyridine, 4-dimethylaminopyridine / 1) CH2Cl2, 0 deg C; 2) DMF, 80 deg C
4: NaCO3 / diethyl ether / 0 °C
5: 1) CF3COOH; 2) Pb(OAc)4 / 1) H2O, 0 deg C; 2) CH2Cl2
6: CrO3, H2SO4 / -15 °C
7: diethyl ether
8: KOH / H2O
View Scheme
(4S,5R)-3-Methyl-5-((E)-(R)-1-methyl-pent-3-enyl)-2-phenyl-oxazolidine-4-carboxylic acid
112920-91-9, 112967-82-5, 112967-85-8, 112967-87-0

(4S,5R)-3-Methyl-5-((E)-(R)-1-methyl-pent-3-enyl)-2-phenyl-oxazolidine-4-carboxylic acid

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
With hydrogenchloride In methanol for 0.5h; Ambient temperature; pH=5; Yield given;
(E)-(2S,3R,4R)-3-Formyloxy-4-methyl-2-[methyl-(2,2,2-trifluoro-acetyl)-amino]-oct-6-enoic acid methyl ester
128254-67-1

(E)-(2S,3R,4R)-3-Formyloxy-4-methyl-2-[methyl-(2,2,2-trifluoro-acetyl)-amino]-oct-6-enoic acid methyl ester

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
With potassium hydroxide In water Yield given;
(4R,5R)-4-hydroxymethyl-3-methyl-5-[(E,1R)-1-methyl-3-pentenyl]-oxazolidin-2-one
372119-48-7

(4R,5R)-4-hydroxymethyl-3-methyl-5-[(E,1R)-1-methyl-3-pentenyl]-oxazolidin-2-one

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: PDC / dimethylformamide / 17 h / 20 °C
2: 70 mg / diethyl ether
3: 80 percent / aq. KOH / 10 h / 80 - 95 °C
View Scheme
(4R,5R)-4-hydroxymethyl-5-((E)-1-methyl-3-pentenyl)-2-phenyl-2-oxazoline

(4R,5R)-4-hydroxymethyl-5-((E)-1-methyl-3-pentenyl)-2-phenyl-2-oxazoline

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: aq. HCl / tetrahydrofuran / 16 h / 20 °C
2: 271 mg / NaHCO3 / H2O; tetrahydrofuran / 2 h / 20 °C
3: 90 percent / imidazole / CH2Cl2 / 2 h / 10 °C
4: NaH / tetrahydrofuran / 48 h / 20 °C
5: NaOMe / methanol / 24 h / 55 - 60 °C
6: 108 mg / aq. HCl / tetrahydrofuran / 3 h / 20 °C
7: PDC / dimethylformamide / 17 h / 20 °C
8: 70 mg / diethyl ether
9: 80 percent / aq. KOH / 10 h / 80 - 95 °C
View Scheme
4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropenyl-oxazolidin-2-one

4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropenyl-oxazolidin-2-one

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1: NaH / tetrahydrofuran / 0 - 20 °C
2: 1,3-bis(diphenylphosphino)propane / Pd2(dibenzylideneacetone)3CHCl3 / tetrahydrofuran / 4 h / 50 °C
3: tetrahydrofuran / 0 - 20 °C
4: 1.53 g / aq. NaOH; Pd(PPh3)4 / tetrahydrofuran / 4 h / 55 - 60 °C
5: 90 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
6: aq. HCl / tetrahydrofuran / 16 h / 20 °C
7: 271 mg / NaHCO3 / H2O; tetrahydrofuran / 2 h / 20 °C
8: 90 percent / imidazole / CH2Cl2 / 2 h / 10 °C
9: NaH / tetrahydrofuran / 48 h / 20 °C
10: NaOMe / methanol / 24 h / 55 - 60 °C
11: 108 mg / aq. HCl / tetrahydrofuran / 3 h / 20 °C
12: PDC / dimethylformamide / 17 h / 20 °C
13: 70 mg / diethyl ether
14: 80 percent / aq. KOH / 10 h / 80 - 95 °C
View Scheme
(4R,5R)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-5-((E)-(R)-1-methyl-pent-3-enyl)-oxazolidin-2-one

(4R,5R)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-methyl-5-((E)-(R)-1-methyl-pent-3-enyl)-oxazolidin-2-one

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 108 mg / aq. HCl / tetrahydrofuran / 3 h / 20 °C
2: PDC / dimethylformamide / 17 h / 20 °C
3: 70 mg / diethyl ether
4: 80 percent / aq. KOH / 10 h / 80 - 95 °C
View Scheme
(4R,5R)-4-tert-butyldimethylsilyloxymethyl-2-phenyl-5-(2-propenyl)-2-oxazoline
372119-42-1

(4R,5R)-4-tert-butyldimethylsilyloxymethyl-2-phenyl-5-(2-propenyl)-2-oxazoline

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: tetrahydrofuran / 0 - 20 °C
2: 1.53 g / aq. NaOH; Pd(PPh3)4 / tetrahydrofuran / 4 h / 55 - 60 °C
3: 90 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
4: aq. HCl / tetrahydrofuran / 16 h / 20 °C
5: 271 mg / NaHCO3 / H2O; tetrahydrofuran / 2 h / 20 °C
6: 90 percent / imidazole / CH2Cl2 / 2 h / 10 °C
7: NaH / tetrahydrofuran / 48 h / 20 °C
8: NaOMe / methanol / 24 h / 55 - 60 °C
9: 108 mg / aq. HCl / tetrahydrofuran / 3 h / 20 °C
10: PDC / dimethylformamide / 17 h / 20 °C
11: 70 mg / diethyl ether
12: 80 percent / aq. KOH / 10 h / 80 - 95 °C
View Scheme
(4R)-4-tert-butoxycarbonylamino-5-tert-butyldimethylsilyloxy-2-methylpent-1-en-3-ol

(4R)-4-tert-butoxycarbonylamino-5-tert-butyldimethylsilyloxy-2-methylpent-1-en-3-ol

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1: NaH / tetrahydrofuran / 0 - 20 °C
2: NaH / tetrahydrofuran / 0 - 20 °C
3: 1,3-bis(diphenylphosphino)propane / Pd2(dibenzylideneacetone)3CHCl3 / tetrahydrofuran / 4 h / 50 °C
4: tetrahydrofuran / 0 - 20 °C
5: 1.53 g / aq. NaOH; Pd(PPh3)4 / tetrahydrofuran / 4 h / 55 - 60 °C
6: 90 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
7: aq. HCl / tetrahydrofuran / 16 h / 20 °C
8: 271 mg / NaHCO3 / H2O; tetrahydrofuran / 2 h / 20 °C
9: 90 percent / imidazole / CH2Cl2 / 2 h / 10 °C
10: NaH / tetrahydrofuran / 48 h / 20 °C
11: NaOMe / methanol / 24 h / 55 - 60 °C
12: 108 mg / aq. HCl / tetrahydrofuran / 3 h / 20 °C
13: PDC / dimethylformamide / 17 h / 20 °C
14: 70 mg / diethyl ether
15: 80 percent / aq. KOH / 10 h / 80 - 95 °C
View Scheme
(4R,5R)-4-tert-butyldimethylsilyloxymethyl-5-((E)-1-methyl-3-pentenyl)-2-phenyl-2-oxazoline

(4R,5R)-4-tert-butyldimethylsilyloxymethyl-5-((E)-1-methyl-3-pentenyl)-2-phenyl-2-oxazoline

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 90 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
2: aq. HCl / tetrahydrofuran / 16 h / 20 °C
3: 271 mg / NaHCO3 / H2O; tetrahydrofuran / 2 h / 20 °C
4: 90 percent / imidazole / CH2Cl2 / 2 h / 10 °C
5: NaH / tetrahydrofuran / 48 h / 20 °C
6: NaOMe / methanol / 24 h / 55 - 60 °C
7: 108 mg / aq. HCl / tetrahydrofuran / 3 h / 20 °C
8: PDC / dimethylformamide / 17 h / 20 °C
9: 70 mg / diethyl ether
10: 80 percent / aq. KOH / 10 h / 80 - 95 °C
View Scheme
(4R)-3-benzoyl-4-tert-butyldimethylsilyloxymethyl-5-(2-propenyl)oxazolidin-2-one

(4R)-3-benzoyl-4-tert-butyldimethylsilyloxymethyl-5-(2-propenyl)oxazolidin-2-one

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 1,3-bis(diphenylphosphino)propane / Pd2(dibenzylideneacetone)3CHCl3 / tetrahydrofuran / 4 h / 50 °C
2: tetrahydrofuran / 0 - 20 °C
3: 1.53 g / aq. NaOH; Pd(PPh3)4 / tetrahydrofuran / 4 h / 55 - 60 °C
4: 90 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
5: aq. HCl / tetrahydrofuran / 16 h / 20 °C
6: 271 mg / NaHCO3 / H2O; tetrahydrofuran / 2 h / 20 °C
7: 90 percent / imidazole / CH2Cl2 / 2 h / 10 °C
8: NaH / tetrahydrofuran / 48 h / 20 °C
9: NaOMe / methanol / 24 h / 55 - 60 °C
10: 108 mg / aq. HCl / tetrahydrofuran / 3 h / 20 °C
11: PDC / dimethylformamide / 17 h / 20 °C
12: 70 mg / diethyl ether
13: 80 percent / aq. KOH / 10 h / 80 - 95 °C
View Scheme
(2R,3R,4R,6E)-2-tert-butoxycarbonylamino-3-benzoyloxy-4-methyloct-6-en-1-ol
372119-46-5

(2R,3R,4R,6E)-2-tert-butoxycarbonylamino-3-benzoyloxy-4-methyloct-6-en-1-ol

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 90 percent / imidazole / CH2Cl2 / 2 h / 10 °C
2: NaH / tetrahydrofuran / 48 h / 20 °C
3: NaOMe / methanol / 24 h / 55 - 60 °C
4: 108 mg / aq. HCl / tetrahydrofuran / 3 h / 20 °C
5: PDC / dimethylformamide / 17 h / 20 °C
6: 70 mg / diethyl ether
7: 80 percent / aq. KOH / 10 h / 80 - 95 °C
View Scheme
(2R,3R,4R,6E)-2-tert-butoxycarbonylamino-3-benzoyloxy-1-tert-butyldimethylsilyloxy-4-methyloct-6-ene
372119-47-6

(2R,3R,4R,6E)-2-tert-butoxycarbonylamino-3-benzoyloxy-1-tert-butyldimethylsilyloxy-4-methyloct-6-ene

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: NaH / tetrahydrofuran / 48 h / 20 °C
2: NaOMe / methanol / 24 h / 55 - 60 °C
3: 108 mg / aq. HCl / tetrahydrofuran / 3 h / 20 °C
4: PDC / dimethylformamide / 17 h / 20 °C
5: 70 mg / diethyl ether
6: 80 percent / aq. KOH / 10 h / 80 - 95 °C
View Scheme
Benzoic acid (E)-(1R,2R)-1-[(R)-1-(tert-butoxycarbonyl-methyl-amino)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-methyl-hex-4-enyl ester

Benzoic acid (E)-(1R,2R)-1-[(R)-1-(tert-butoxycarbonyl-methyl-amino)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-methyl-hex-4-enyl ester

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: NaOMe / methanol / 24 h / 55 - 60 °C
2: 108 mg / aq. HCl / tetrahydrofuran / 3 h / 20 °C
3: PDC / dimethylformamide / 17 h / 20 °C
4: 70 mg / diethyl ether
5: 80 percent / aq. KOH / 10 h / 80 - 95 °C
View Scheme
Benzoic acid (E)-(R)-1-((R)-1-amino-2-hydroxy-ethyl)-2-methyl-hex-4-enyl ester; hydrochloride

Benzoic acid (E)-(R)-1-((R)-1-amino-2-hydroxy-ethyl)-2-methyl-hex-4-enyl ester; hydrochloride

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 271 mg / NaHCO3 / H2O; tetrahydrofuran / 2 h / 20 °C
2: 90 percent / imidazole / CH2Cl2 / 2 h / 10 °C
3: NaH / tetrahydrofuran / 48 h / 20 °C
4: NaOMe / methanol / 24 h / 55 - 60 °C
5: 108 mg / aq. HCl / tetrahydrofuran / 3 h / 20 °C
6: PDC / dimethylformamide / 17 h / 20 °C
7: 70 mg / diethyl ether
8: 80 percent / aq. KOH / 10 h / 80 - 95 °C
View Scheme
(4R,5R)-5-[(R)-2-(9-Bora-bicyclo[3.3.1]non-9-yl)-1-methyl-ethyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-4,5-dihydro-oxazole

(4R,5R)-5-[(R)-2-(9-Bora-bicyclo[3.3.1]non-9-yl)-1-methyl-ethyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-phenyl-4,5-dihydro-oxazole

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 1.53 g / aq. NaOH; Pd(PPh3)4 / tetrahydrofuran / 4 h / 55 - 60 °C
2: 90 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
3: aq. HCl / tetrahydrofuran / 16 h / 20 °C
4: 271 mg / NaHCO3 / H2O; tetrahydrofuran / 2 h / 20 °C
5: 90 percent / imidazole / CH2Cl2 / 2 h / 10 °C
6: NaH / tetrahydrofuran / 48 h / 20 °C
7: NaOMe / methanol / 24 h / 55 - 60 °C
8: 108 mg / aq. HCl / tetrahydrofuran / 3 h / 20 °C
9: PDC / dimethylformamide / 17 h / 20 °C
10: 70 mg / diethyl ether
11: 80 percent / aq. KOH / 10 h / 80 - 95 °C
View Scheme
(2R)-2-methylhex-4-yn-1-ol
158220-67-8

(2R)-2-methylhex-4-yn-1-ol

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1.)(COCl)2, DMSO, 2.) Et3N / -78 °C
2: 63 percent / KHMDS, 18-crown-6 / tetrahydrofuran / 1 h / -78 °C
3: 82 percent / DIBAL-H / diethyl ether; hexane / 4 h / -78 °C
4: 1.) molecular sieves 4A, L-(+)-diethyltartrate, Ti(OiPr)4, 2.) tert-butyl hydroperoxide / 1.) CH2Cl2, -20 deg C, 3 min, 2.) CH2Cl2, -20 deg C, 60 h
5: 75 percent / pyridium dichromate / dimethylformamide / 48 h / Ambient temperature
7: 70 percent / Li, NH3(liq.) / 0.08 h / -20 °C
View Scheme
(2R)-2-methyl-4-hexyn-1-al
158220-68-9

(2R)-2-methyl-4-hexyn-1-al

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 63 percent / KHMDS, 18-crown-6 / tetrahydrofuran / 1 h / -78 °C
2: 82 percent / DIBAL-H / diethyl ether; hexane / 4 h / -78 °C
3: 1.) molecular sieves 4A, L-(+)-diethyltartrate, Ti(OiPr)4, 2.) tert-butyl hydroperoxide / 1.) CH2Cl2, -20 deg C, 3 min, 2.) CH2Cl2, -20 deg C, 60 h
4: 75 percent / pyridium dichromate / dimethylformamide / 48 h / Ambient temperature
6: 70 percent / Li, NH3(liq.) / 0.08 h / -20 °C
View Scheme
(2Z,4R) 4-methyl oct-6-yn-2-en-1-ol
158220-63-4

(2Z,4R) 4-methyl oct-6-yn-2-en-1-ol

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) molecular sieves 4A, L-(+)-diethyltartrate, Ti(OiPr)4, 2.) tert-butyl hydroperoxide / 1.) CH2Cl2, -20 deg C, 3 min, 2.) CH2Cl2, -20 deg C, 60 h
2: 75 percent / pyridium dichromate / dimethylformamide / 48 h / Ambient temperature
4: 70 percent / Li, NH3(liq.) / 0.08 h / -20 °C
View Scheme
(2R,3R,4R) 2,3-epoxy-4-methyl oct-6-ynoic acid
158220-65-6

(2R,3R,4R) 2,3-epoxy-4-methyl oct-6-ynoic acid

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: 70 percent / Li, NH3(liq.) / 0.08 h / -20 °C
View Scheme
(S)-4-Benzyl-3-((R)-2-methyl-hex-4-ynoyl)-oxazolidin-2-one
158220-66-7

(S)-4-Benzyl-3-((R)-2-methyl-hex-4-ynoyl)-oxazolidin-2-one

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 74 percent / LiAlH4 / diethyl ether / 0 °C
2: 1.)(COCl)2, DMSO, 2.) Et3N / -78 °C
3: 63 percent / KHMDS, 18-crown-6 / tetrahydrofuran / 1 h / -78 °C
4: 82 percent / DIBAL-H / diethyl ether; hexane / 4 h / -78 °C
5: 1.) molecular sieves 4A, L-(+)-diethyltartrate, Ti(OiPr)4, 2.) tert-butyl hydroperoxide / 1.) CH2Cl2, -20 deg C, 3 min, 2.) CH2Cl2, -20 deg C, 60 h
6: 75 percent / pyridium dichromate / dimethylformamide / 48 h / Ambient temperature
8: 70 percent / Li, NH3(liq.) / 0.08 h / -20 °C
View Scheme
(2S,3R,4R) 2,3-epoxy-4-methyl oct-6-yn-1-ol
158220-64-5

(2S,3R,4R) 2,3-epoxy-4-methyl oct-6-yn-1-ol

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 75 percent / pyridium dichromate / dimethylformamide / 48 h / Ambient temperature
3: 70 percent / Li, NH3(liq.) / 0.08 h / -20 °C
View Scheme
methyl (2Z,4R) 4-methyl oct-6-yn-2-enoate
158220-69-0

methyl (2Z,4R) 4-methyl oct-6-yn-2-enoate

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 82 percent / DIBAL-H / diethyl ether; hexane / 4 h / -78 °C
2: 1.) molecular sieves 4A, L-(+)-diethyltartrate, Ti(OiPr)4, 2.) tert-butyl hydroperoxide / 1.) CH2Cl2, -20 deg C, 3 min, 2.) CH2Cl2, -20 deg C, 60 h
3: 75 percent / pyridium dichromate / dimethylformamide / 48 h / Ambient temperature
5: 70 percent / Li, NH3(liq.) / 0.08 h / -20 °C
View Scheme
(5R)-3-methyl-5-<(1R,3E)-1-methyl-3-pentenyl>-2-oxo-4-oxazolidine-carbonitrile
81143-07-9, 81202-45-1, 84926-84-1, 89362-99-2

(5R)-3-methyl-5-<(1R,3E)-1-methyl-3-pentenyl>-2-oxo-4-oxazolidine-carbonitrile

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 90 percent / K2CO3 / H2O / 6 h / Ambient temperature
2: 95 percent / 1 N HCl / aq. ethanol / 2 h / Ambient temperature
3: 90 percent / 2 N KOH / 3 h / 80 °C
View Scheme
Multi-step reaction with 4 steps
1: 90 percent / K2CO3 / H2O / 6 h / Ambient temperature
2: 95 percent / 1 N HCl / aq. ethanol / 2 h / Ambient temperature
3: 90 percent / 0.1 N KOH / dioxane / 1 h / Ambient temperature
4: 94 percent / 2 N KOH / 3 h / 80 °C / 2) pH=5
View Scheme
(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

acetone
67-64-1

acetone

(4S,5R,1'R,3'E)-2,2,3-trimethyl-5-(1'-methyl-3'-pentenyl)-4-oxazolidinecarboxylic acid
81135-31-1

(4S,5R,1'R,3'E)-2,2,3-trimethyl-5-(1'-methyl-3'-pentenyl)-4-oxazolidinecarboxylic acid

Conditions
ConditionsYield
100%
for 20h; Heating;
for 24h; Heating;
In acetone for 24h; Heating;
(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

H-MeBmt-Abu-Sar-MeLeu-Val-MeLeu-Phe-OBzl
1027283-80-2

H-MeBmt-Abu-Sar-MeLeu-Val-MeLeu-Phe-OBzl

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 24 h / Heating
2: N-methylmorpholine, 1-hydroxybenzotriazole, DCC / acetone; tetrahydrofuran / 20 h / Ambient temperature
3: 1 N aq. HCl / methanol / 15 h / Heating
View Scheme
(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

H-MeBmt-Abu-(D)-MeAla-MeLeu-Val-MeLeu-Phe-OBzl
1027556-01-9

H-MeBmt-Abu-(D)-MeAla-MeLeu-Val-MeLeu-Phe-OBzl

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 24 h / Heating
2: N-methylmorpholine, 1-hydroxybenzotriazole, DCC / acetone; tetrahydrofuran / 20 h / Ambient temperature
3: 1 N aq. HCl / methanol / 15 h / Heating
View Scheme
(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

C55H85N7O9

C55H85N7O9

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 24 h / Heating
2: N-methylmorpholine, 1-hydroxybenzotriazole, DCC / acetone; tetrahydrofuran / 20 h / Ambient temperature
View Scheme
(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid
59865-23-5

(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-methylamino-6-octenoic acid

C56H87N7O9

C56H87N7O9

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 24 h / Heating
2: N-methylmorpholine, 1-hydroxybenzotriazole, DCC / acetone; tetrahydrofuran / 20 h / Ambient temperature
View Scheme

59865-23-5Relevant articles and documents

Application of the gold(I)-catalyzed aldol reaction to a stereoselective synthesis of (2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)oct-6-enoic acid (= MeBmt1)), cyclosporin's unusual amino acid

Togni,Pastor,Rihs

, p. 1471 - 1478 (1989)

-

Stereoselective synthesis of MeBmt and methyl (4R,5S)-5-isopropyl-2-phenyloxazoline-4-carboxylate by a Pd-catalyzed equilibration

Cook,Shanker

, p. 6818 - 6822 (2007/10/03)

-

A Stereoselective Synthesis of MeBmt Employing a New Chiral Glycine Enolate Derivative

Blaser, Denis,Ko, Soo Y.,Seebach, Dieter

, p. 6230 - 6233 (2007/10/02)

-

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