(3R,4S,E)-4-(tert-butyldimethylsilyloxy)-1-phenylpent-1-en-3-ol

Base Information

• Chemical Name: (3R,4S,E)-4-(tert-butyldimethylsilyloxy)-1-phenylpent-1-en-3-ol
• CAS No.: 1219619-36-9
• Molecular Formula: C₁₇H₂₈O₂Si
• Molecular Weight: 292.494
• Mol file: 1219619-36-9.mol

Synonyms:(3R,4S,E)-4-(tert-butyldimethylsilyloxy)-1-phenylpent-1-en-3-ol

Chemical Property of (3R,4S,E)-4-(tert-butyldimethylsilyloxy)-1-phenylpent-1-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,E)-4-(tert-butyldimethylsilyloxy)-1-phenylpent-1-en-3-ol

There total 5 articles about (3R,4S,E)-4-(tert-butyldimethylsilyloxy)-1-phenylpent-1-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:

Diethyl-((E)-styryl)-borane (42206-19-9) + (S)-2-tert-butyl-dimethyl-silanyloxy propanal (87727-28-4) → (3R,4S,E)-4-(tert-butyldimethylsilyloxy)-1-phenylpent-1-en-3-ol (1219619-36-9) + (3S,4S,E)-4-(tert-butyldimethylsilyloxy)-1-phenylpent-1-en-3-ol (1219619-07-4)

Guidance literature:

Diethyl-((E)-styryl)-borane; With dimethyl zinc(II); In dichloromethane; toluene; at -78 ℃; Inert atmosphere;

(S)-2-tert-butyl-dimethyl-silanyloxy propanal; In dichloromethane; toluene; at -30 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ja910717p

Reference yield:

benzaldehyde (100-52-7) → (3R,4S,E)-4-(tert-butyldimethylsilyloxy)-1-phenylpent-1-en-3-ol (1219619-36-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 52 percent / benzene

2: acidic hydrolysis

3: silylation

4: sodium borohydride

With sodium tetrahydroborate; In benzene;

DOI:10.1016/S0040-4039(01)91269-9

Reference yield:

(E)-(S)-4-Hydroxy-1-phenyl-pent-1-en-3-one (103635-88-7) → (3R,4S,E)-4-(tert-butyldimethylsilyloxy)-1-phenylpent-1-en-3-ol (1219619-36-9)

Guidance literature:

Multi-step reaction with 2 steps

1: silylation

2: sodium borohydride

With sodium tetrahydroborate;

DOI:10.1016/S0040-4039(01)91269-9

upstream raw materials:

(S,E)-4-(tert-butyldimethylsilyloxy)-1-phenylpent-1-en-3-one

(E)-(S)-4-Hydroxy-1-phenyl-pent-1-en-3-one

Acetic acid (E)-(S)-1-methyl-2-oxo-4-phenyl-but-3-enyl ester

benzaldehyde

Downstream raw materials:

2-Phenyl-4-hydroxy-butyraldehyd

(+/-)-2-phenyl-1,4-butanediol

(E)-(3S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-phenyl-hept-4-enoic acid ethyl ester