(2R,6S)-3-Benzenesulfonyl-1-(tert-butyl-diphenyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2,5,5-trimethyl-oct-7-en-4-ol

Base Information

• Chemical Name: (2R,6S)-3-Benzenesulfonyl-1-(tert-butyl-diphenyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2,5,5-trimethyl-oct-7-en-4-ol
• CAS No.: 861119-15-5
• Molecular Formula: C₄₁H₅₂O₆SSi
• Molecular Weight: 701.012
• Mol file: 861119-15-5.mol

Synonyms:(2R,6S)-3-Benzenesulfonyl-1-(tert-butyl-diphenyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2,5,5-trimethyl-oct-7-en-4-ol

Chemical Property of (2R,6S)-3-Benzenesulfonyl-1-(tert-butyl-diphenyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2,5,5-trimethyl-oct-7-en-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6S)-3-Benzenesulfonyl-1-(tert-butyl-diphenyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2,5,5-trimethyl-oct-7-en-4-ol

There total 11 articles about (2R,6S)-3-Benzenesulfonyl-1-(tert-butyl-diphenyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2,5,5-trimethyl-oct-7-en-4-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: 98.0%

(3S)-3-[(4-methoxyphenyl)methoxy]-2,2-dimethylpent-4-enal (861118-37-8) + phenyl (2R)-3-(tert-butyldiphenylsilyl)oxy-2-methylpropyl sulfone (158812-78-3) → (2R,6S)-3-Benzenesulfonyl-1-(tert-butyl-diphenyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2,5,5-trimethyl-oct-7-en-4-ol (861119-15-5)

Guidance literature:

phenyl (2R)-3-(tert-butyldiphenylsilyl)oxy-2-methylpropyl sulfone; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;

(3S)-3-[(4-methoxyphenyl)methoxy]-2,2-dimethylpent-4-enal; In tetrahydrofuran; hexane; at -50 ℃; for 1h;

DOI:10.1021/jo0503862

Reference yield:

(3S)-3-[(4-methoxyphenyl)methoxy]-2,2-dimethylpent-4-en-1-ol (861119-09-7) → (2R,6S)-3-Benzenesulfonyl-1-(tert-butyl-diphenyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2,5,5-trimethyl-oct-7-en-4-ol (861119-15-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 98 percent / oxalyl chloride DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

2.2: 98 percent / tetrahydrofuran; hexane / 1 h / -50 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1.1: Swern oxidation;

DOI:10.1021/jo0503862

Reference yield:

(S)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol (95514-04-8,129029-85-2,120346-83-0) → (2R,6S)-3-Benzenesulfonyl-1-(tert-butyl-diphenyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2,5,5-trimethyl-oct-7-en-4-ol (861119-15-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 90 percent / n-Bu₃P / benzene / 2.5 h / 20 °C

2.1: 82 percent / Oxone / tetrahydrofuran; methanol; H₂O / 24 h / 20 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

3.2: 98 percent / tetrahydrofuran; hexane / 1 h / -50 °C

With Oxone; n-butyllithium; tributylphosphine; In tetrahydrofuran; methanol; hexane; water; benzene;

DOI:10.1021/jo0503862

upstream raw materials:

(3S)-3-[(4-methoxyphenyl)methoxy]-2,2-dimethylpent-4-enal

phenyl (2R)-3-(tert-butyldiphenylsilyl)oxy-2-methylpropyl sulfone

(3S)-3-[(4-methoxyphenyl)methoxy]-2,2-dimethylpent-4-en-1-ol

(S)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol

Downstream raw materials:

(2R,6S)-3-Benzenesulfonyl-1-(tert-butyl-diphenyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2,5,5-trimethyl-oct-7-en-4-one

tert-Butyl-[(S)-2-methyl-3-((4S,6S)-2,2,5,5-tetramethyl-6-vinyl-[1,3]dioxan-4-yl)-propoxy]-diphenyl-silane

(3S,7S)-8-(tert-butyldiphenylsilyl)oxy-3-[(4-methoxyphenyl)methoxy]-4,4,7-trimethyloct-1-en-5-one