(3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

Base Information

• Chemical Name: (3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS No.: 114738-04-4
• Molecular Formula: C24H32O5Si
• Molecular Weight: 428.601
• Mol file: 114738-04-4.mol

Synonyms:(3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

Chemical Property of (3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

Chemical Property:

• PSA: 57.15000
• LogP: 2.80030

Purity/Quality:

≥99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

There total 16 articles about (3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[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: 84.0%

5-O-(tert-butyldiphenylsilyl)-D-arabinose diethyldithioacetal (162517-90-0) → (3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (114738-04-4)

Guidance literature:

5-O-(tert-butyldiphenylsilyl)-D-arabinose diethyldithioacetal; With mercury dichloride; mercury(II) oxide; In acetone;

With hydrogen cation; copper(II) sulfate; In acetone;

DOI:10.1016/S0040-4039(01)00376-8

Reference yield: 76.0%

(3S,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2,3,4-triol (168608-39-7) + 2,2-dimethoxy-propane (77-76-9) → (3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (114738-04-4)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 4 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201300887

Reference yield: 74.0%

(3S,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2,3,4-triol (168608-39-7) + acetone (67-64-1) → (3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (114738-04-4)

Guidance literature:

With sulfuric acid; copper(II) sulfate; for 8h; Inert atmosphere;

DOI:10.1016/j.carres.2013.07.017

upstream raw materials:

5-O-(tert-butyldiphenylsilyl)-D-arabinose diethyldithioacetal

D-Arabinose

acetone

(3S,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2,3,4-triol

Downstream raw materials:

(3aS,5R,6R,6aS)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

3-O-acetyl-5-O-tert-butyldiphenylsilyl-1,2-O,O-isopropylidene-β-D-arabinofuranose

(((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methoxy)(tert-butyl)diphenylsilane

5-azido-3-O-benzyl-1,2-O-isopropylidene-β-D-arabinofuranose