(2S,3R,4R)-4-(Benzhydryl-dimethyl-silanyl)-2-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-vinyl-heptan-3-ol

Base Information

• Chemical Name: (2S,3R,4R)-4-(Benzhydryl-dimethyl-silanyl)-2-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-vinyl-heptan-3-ol
• CAS No.: 871268-94-9
• Molecular Formula: C₃₇H₅₄O₃Si₂
• Molecular Weight: 603.005
• Mol file: 871268-94-9.mol

Synonyms:(2S,3R,4R)-4-(Benzhydryl-dimethyl-silanyl)-2-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-vinyl-heptan-3-ol

Chemical Property of (2S,3R,4R)-4-(Benzhydryl-dimethyl-silanyl)-2-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-vinyl-heptan-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R)-4-(Benzhydryl-dimethyl-silanyl)-2-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-vinyl-heptan-3-ol

There total 5 articles about (2S,3R,4R)-4-(Benzhydryl-dimethyl-silanyl)-2-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-vinyl-heptan-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: 52.0%

[(Z)-3-(Benzhydryl-dimethyl-silanyl)-hex-2-enyl]-bis-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borane + (2S)-2-benzyloxy-3-[tert-butyl(dimethyl)silyloxy]-propanal (163275-51-2) → (2S,3S,4S)-4-(Benzhydryl-dimethyl-silanyl)-2-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-vinyl-heptan-3-ol + (2S,3R,4R)-4-(Benzhydryl-dimethyl-silanyl)-2-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-vinyl-heptan-3-ol (871268-94-9)

Guidance literature:

In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/ol052321r

Reference yield:

methanesulfonic acid 3-(benzhydryl-dimethyl-silanyl)-prop-2-ynyl ester (871268-92-7) → (2S,3R,4R)-4-(Benzhydryl-dimethyl-silanyl)-2-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-vinyl-heptan-3-ol (871268-94-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LiBr; CuBr*SMe₂ / tetrahydrofuran; diethyl ether / 1 h / -10 °C

1.2: 4.79 g / tetrahydrofuran; diethyl ether / 1 h / -60 - 20 °C

2.1: tetrahydrofuran / 7 h / -50 °C

3.1: 52 percent / tetrahydrofuran / -78 - 20 °C

With copper(I) bromide dimethylsulfide complex; lithium bromide; In tetrahydrofuran; diethyl ether;

DOI:10.1021/ol052321r

Reference yield:

(diphenylmethyl)dimethylchlorosilane (132455-95-9) → (2S,3R,4R)-4-(Benzhydryl-dimethyl-silanyl)-2-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-vinyl-heptan-3-ol (871268-94-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

1.2: tetrahydrofuran; hexane / 1 h / 0 °C

2.1: 6.8 g / MeOH; p-TsOH*H₂O / 0 - 20 °C

3.1: pyridine / CH₂Cl₂ / 1 h / 0 °C

4.1: LiBr; CuBr*SMe₂ / tetrahydrofuran; diethyl ether / 1 h / -10 °C

4.2: 4.79 g / tetrahydrofuran; diethyl ether / 1 h / -60 - 20 °C

5.1: tetrahydrofuran / 7 h / -50 °C

6.1: 52 percent / tetrahydrofuran / -78 - 20 °C

With pyridine; methanol; n-butyllithium; copper(I) bromide dimethylsulfide complex; toluene-4-sulfonic acid; lithium bromide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1021/ol052321r

upstream raw materials:

(2S)-2-benzyloxy-3-[tert-butyl(dimethyl)silyloxy]-propanal

benzhydryl-dimethyl-(1-propyl-propa-1,2-dienyl)-silane

methanesulfonic acid 3-(benzhydryl-dimethyl-silanyl)-prop-2-ynyl ester

(diphenylmethyl)dimethylchlorosilane

Downstream raw materials:

C₄₃H₆₈O₃Si₃