(2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-4-methyl-hex-5-en-3-ol

Base Information

• Chemical Name: (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-4-methyl-hex-5-en-3-ol
• CAS No.: 848035-35-8
• Molecular Formula: C₂₄H₃₄O₃Si
• Molecular Weight: 398.618
• Mol file: 848035-35-8.mol

Synonyms:(2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-4-methyl-hex-5-en-3-ol

Chemical Property of (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-4-methyl-hex-5-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-4-methyl-hex-5-en-3-ol

There total 5 articles about (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-4-methyl-hex-5-en-3-ol 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: 87.0%

tri-n-butylcrotyltin (35998-93-7) + 3-(tert-butyl-diphenyl-silanyloxy)-2-methoxy-propionaldehyde (494834-74-1) → (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-4-methyl-hex-5-en-3-ol (848035-35-8)

Guidance literature:

3-(tert-butyl-diphenyl-silanyloxy)-2-methoxy-propionaldehyde; With magnesium bromide; In dichloromethane; at -21 ℃; for 0.666667h;

tri-n-butylcrotyltin; In dichloromethane; at -60 ℃; for 7h; Further stages.;

DOI:10.1016/j.tet.2007.02.107

Reference yield:

tri-n-butylcrotyltin (35998-93-7) + (2R)-3-(tert-butyldiphenyl-silyloxy)-2-methoxy-propan-1-ol (494834-73-0) → (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-4-methyl-hex-5-en-3-ol (848035-35-8)

Guidance literature:

(2R)-3-(tert-butyldiphenyl-silyloxy)-2-methoxy-propan-1-ol; With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;

tri-n-butylcrotyltin; With magnesium bromide; In dichloromethane; at -60 ℃;

DOI:10.1002/ejoc.200600760

Reference yield:

(2S)-methyl 3-(tert-butyldiphenylsilyloxy)-2-methoxy-propionate (918868-38-9) → (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-methoxy-4-methyl-hex-5-en-3-ol (848035-35-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 90 percent / DIBAL-H / CH₂Cl₂; hexane / 2.5 h / 20 °C

2.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: MgBr₂*OEt₂ / CH₂Cl₂ / 0.67 h / -21 °C

3.2: 87 percent / CH₂Cl₂ / 7 h / -60 °C

With oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; magnesium bromide; In hexane; dichloromethane; 2.1: Swern oxidation;

DOI:10.1016/j.tet.2007.02.107

upstream raw materials:

tri-n-butylcrotyltin

(2R)-3-(tert-butyldiphenyl-silyloxy)-2-methoxy-propan-1-ol

3-(tert-butyl-diphenyl-silanyloxy)-2-methoxy-propionaldehyde

(2S)-methyl 3-(tert-butyldiphenylsilyloxy)-2-methoxy-propionate

Downstream raw materials:

2-methyl-acrylic acid 1-[2-(tert-butyl-diphenyl-silanyloxy)-1-methoxy-ethyl]-2-methyl-but-3-enyl ester

(2S,3S,4R)-3-(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenyl-silyloxy)-2-methoxy-4-methyl-hex-5-ene

5-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-2,4-dimethyl-hept-2-enal

5-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-2,4-dimethyl-hept-2-en-1-ol