(3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol

Base Information

• Chemical Name: (3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol
• CAS No.: 103763-14-0
• Molecular Formula: C₂₄H₃₂O₅Si
• Molecular Weight: 428.601
• Mol file: 103763-14-0.mol

Synonyms:(3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol

Chemical Property of (3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol

There total 13 articles about (3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-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: 86.0%

5-O-tert-butyldiphenylsilyl-α,β-L-arabinofuranose (103763-12-8,103763-13-9) + acetone (67-64-1) → (3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol (103763-14-0)

Guidance literature:

With camphor-10-sulfonic acid; copper(II) sulfate; at 20 ℃;

DOI:10.1021/acs.jnatprod.7b00212

Reference yield: 78.0%

L-(+)-arabinose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) + acetone (67-64-1) + tert-butylchlorodiphenylsilane (58479-61-1) → (3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol (103763-14-0)

Guidance literature:

L-(+)-arabinose; tert-butylchlorodiphenylsilane; With 1H-imidazole; In N,N-dimethyl-formamide; at 60 ℃; for 2h;

acetone; With camphor-10-sulfonic acid; copper(II) sulfate; at 20 ℃; for 4h; pH=2; Further stages.;

DOI:10.1016/j.tetasy.2008.03.030

Reference yield: 76.0%

5-O-tert-butyldiphenylsilyl-α,β-L-arabinofuranose (103763-12-8,103763-13-9) → (3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol (103763-14-0)

Guidance literature:

With dmap; toluene-4-sulfonic acid; In dichloromethane; at 4 ℃; for 14h;

upstream raw materials:

5-O-tert-butyldiphenylsilyl-α,β-L-arabinofuranose

2,2-dimethoxy-propane

acetone

D-Arabinose

Downstream raw materials:

5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-3-O-(phenoxythiocarbonyl)-β-L-arabinofuranose

3-O-benzyl-1,2-O-isopropylidene-β-L-arabinofuranose

1,2-O-isopropylidene-3,5-di-O-benzyl-β-L-arabinofuranose

C₃₅H₄₀O₅Si