Methanesulfonic acid (E)-(2S,3R,4R)-2-benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hept-5-enyl ester

Base Information

• Chemical Name: Methanesulfonic acid (E)-(2S,3R,4R)-2-benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hept-5-enyl ester
• CAS No.: 213454-13-8
• Molecular Formula: C₂₂H₃₇NO₇SSi
• Molecular Weight: 487.69
• Mol file: 213454-13-8.mol

Synonyms:Methanesulfonic acid (E)-(2S,3R,4R)-2-benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hept-5-enyl ester

Chemical Property of Methanesulfonic acid (E)-(2S,3R,4R)-2-benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hept-5-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (E)-(2S,3R,4R)-2-benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hept-5-enyl ester

There total 5 articles about Methanesulfonic acid (E)-(2S,3R,4R)-2-benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hept-5-enyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde (117833-92-8) → Methanesulfonic acid (E)-(2S,3R,4R)-2-benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hept-5-enyl ester (213454-13-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: MgBr₂*Et₂O / -20 °C

1.2: 95 percent / CH₂Cl₂ / 25 °C

2.1: 93 percent / camphorsulfonic acid; ethylene glycol / tetrahydrofuran / 50 °C

3.1: Et₃N

With camphor-10-sulfonic acid; ethylene glycol; triethylamine; magnesium bromide; In tetrahydrofuran; 1.1: complexation / 1.2: Addition / 2.1: Ring cleavage / 3.1: mesylation;

DOI:10.1021/ja992274w

Reference yield:

(S)-(Z)-1-((tert-Butyldimethylsilyl)oxy)-3-(tri-n-butylstannyl)-1-butene → Methanesulfonic acid (E)-(2S,3R,4R)-2-benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hept-5-enyl ester (213454-13-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: MgBr₂*Et₂O / -20 °C

1.2: 95 percent / CH₂Cl₂ / 25 °C

2.1: 93 percent / camphorsulfonic acid; ethylene glycol / tetrahydrofuran / 50 °C

3.1: Et₃N

With camphor-10-sulfonic acid; ethylene glycol; triethylamine; magnesium bromide; In tetrahydrofuran; 1.1: complexation / 1.2: Addition / 2.1: Ring cleavage / 3.1: mesylation;

DOI:10.1021/ja992274w

Reference yield:

(S)-4-[(E)-(1R,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-pent-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (213454-11-6) → Methanesulfonic acid (E)-(2S,3R,4R)-2-benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-hept-5-enyl ester (213454-13-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / camphorsulfonic acid; ethylene glycol / tetrahydrofuran / 50 °C

2: Et₃N

With camphor-10-sulfonic acid; ethylene glycol; triethylamine; In tetrahydrofuran; 1: Ring cleavage / 2: mesylation;

DOI:10.1021/ja992274w

upstream raw materials:

methanesulfonyl chloride

[(E)-(1S,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-1-hydroxymethyl-hex-4-enyl]-carbamic acid benzyl ester

(4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde

(S)-4-[(E)-(1R,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-pent-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Downstream raw materials:

Phenyl-acetic acid (E)-(1R,2R)-1-((S)-1-benzyloxycarbonylamino-2-methanesulfonyloxy-ethyl)-2-(tert-butyl-dimethyl-silanyloxy)-pent-3-enyl ester

Methoxy-acetic acid (E)-(1R,2R)-1-((S)-1-benzyloxycarbonylamino-2-methanesulfonyloxy-ethyl)-2-(tert-butyl-dimethyl-silanyloxy)-pent-3-enyl ester

(S)-2-((E)-(1R,2S)-2-Acetoxy-4-acetylamino-3-bromo-1-hydroxy-4-methoxycarbonyl-but-3-enyl)-aziridine-1-carboxylic acid benzyl ester

(S)-2-((E)-(1R,2S)-2-Acetoxy-4-acetylamino-3-bromo-4-methoxycarbonyl-1-trimethylsilanyloxy-but-3-enyl)-aziridine-1-carboxylic acid benzyl ester