(2S,3S,4S)-5-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-3,4-dimethyl-pentan-2-ol

Base Information

• Chemical Name: (2S,3S,4S)-5-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-3,4-dimethyl-pentan-2-ol
• CAS No.: 158817-26-6
• Molecular Formula: C₂₀H₃₆O₃Si
• Molecular Weight: 352.59
• Mol file: 158817-26-6.mol

Synonyms:(2S,3S,4S)-5-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-3,4-dimethyl-pentan-2-ol

Chemical Property of (2S,3S,4S)-5-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-3,4-dimethyl-pentan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-5-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-3,4-dimethyl-pentan-2-ol

There total 2 articles about (2S,3S,4S)-5-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-3,4-dimethyl-pentan-2-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: 66.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2S,3S,4S)-5-Benzyloxy-3,4-dimethyl-pentane-1,2-diol → (2S,3S,4S)-5-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-3,4-dimethyl-pentan-2-ol (158817-26-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 17h;

DOI:10.1246/cl.1994.1611

Reference yield:

((2R,3R)-3-((R)-1-(Benzyloxy)propan-2-yl)oxiran-2-yl)methanol → (2S,3S,4S)-5-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-3,4-dimethyl-pentan-2-ol (158817-26-6)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂; hexane / 17 h / Ambient temperature

2: 1.18 g / NEt₃, DMAP / CH₂Cl₂ / 17 h / Ambient temperature

With dmap; triethylamine; In hexane; dichloromethane;

DOI:10.1016/S0040-4020(97)10253-8

Reference yield: 93.0%

(2S,3S,4S)-5-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-3,4-dimethyl-pentan-2-ol (158817-26-6) → (S)-4-((1S,2S)-3-Benzyloxy-1,2-dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolane (158817-27-7)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; for 36h; Ambient temperature;

DOI:10.1016/S0040-4020(97)10253-8

upstream raw materials:

tert-butyldimethylsilyl chloride

Downstream raw materials:

(S)-4-((1S,2S)-3-Benzyloxy-1,2-dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolane

Benzoic acid (Z)-(1S,4R)-1-[(1S,2S)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methyl-propyl]-6-(4-methoxy-benzyloxy)-4-methyl-hex-2-enyl ester

(4S,5S,6R,1'R,1''S,2''S,3''S)-2,2-dimethyl-5-p-methoxybenzyloxy-4-(3'-p-methoxybenzyloxy-1'-methylpropyl)-6-(1'',2''-dimethyl-3'',4''-epoxybutyl)-1,3-dioxane

(4S,5S,6R,1'R,1''S,2''S,3''S)-2,2-dimethyl-5-p-methoxybenzyloxy-4-(3'-p-methoxybenzyloxy-1'-methylpropyl)-6-(1'',2''-dimethyl-3'',4''-dihydroxybutyl)-1,3-dioxane