(2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol

Base Information

• Chemical Name: (2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol
• CAS No.: 201472-26-6
• Molecular Formula: C₂₁H₂₈O₃Si
• Molecular Weight: 356.537
• Mol file: 201472-26-6.mol

Synonyms:(2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol

Chemical Property of (2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol

There total 7 articles about (2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-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: 99.0%

(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one (102717-29-3) → (2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol (201472-26-6)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 1h;

DOI:10.1016/S0957-4166(00)00351-7

Reference yield: 93.0%

(S)-1-((tert-butyldiphenylsilyl)oxy)hex-5-en-2-ol (313963-29-0) → (2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol (201472-26-6)

Guidance literature:

(S)-1-((tert-butyldiphenylsilyl)oxy)hex-5-en-2-ol; With ozone; In dichloromethane; at -78 ℃; for 0.25h;

With triphenylphosphine; In dichloromethane; at -78 - 20 ℃; for 14h;

DOI:10.1002/1521-3773(20001016)39:20<3622::AID-ANIE3622>3.0.CO;2-H

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → (2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol (201472-26-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 0 - 20 °C

2: 95 percent / DIBAL / CH₂Cl₂ / 2 h / -78 °C

With dmap; diisobutylaluminium hydride; triethylamine; In dichloromethane;

DOI:10.1016/j.tetlet.2007.03.014

upstream raw materials:

(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one

(S)-1-((tert-butyldiphenylsilyl)oxy)hex-5-en-2-ol

tert-butyl[(2S)-oxiran-2-ylmethoxy]diphenylsilane

allylmagnesium bromide

Downstream raw materials:

1-acetoxy-2,3-dideoxy-5-O-<(1,1-dimethylethyl)diphenylsilyl>-D-glycero-pentofuranose

2,3-dideoxy-5-O-<(1,1-dimethylethyl)diphenylsilyl>-α-D-glycero-pentofuranosyl chloride

(1S)-1-<<(tert-butyldiphenylsilyl)oxy>methyl>-2,3-dihydrofuran

(2S,2'S,5'S)-5'-(tert-Butyl-diphenyl-silanyloxymethyl)-2',3',4',5'-tetrahydro-2H-[2,2']bifuranyl-5-one