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

Base Information

• Chemical Name: (((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methoxy)(tert-butyl)diphenylsilane
• CAS No.: 168103-00-2
• Molecular Formula: C₃₁H₃₈O₅Si
• Molecular Weight: 518.725
• Mol file: 168103-00-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methoxy)(tert-butyl)diphenylsilane 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: 93.0%

benzyl bromide (100-39-0) + (3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (114738-04-4) → (((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methoxy)(tert-butyl)diphenylsilane (168103-00-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 3h;

DOI:10.1002/ejoc.201300887

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methoxy)(tert-butyl)diphenylsilane (168103-00-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 60 °C

2: camphor-10-sulfonic acid; copper(II) sulfate / pH 2

3: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 °C

With 1H-imidazole; camphor-10-sulfonic acid; sodium hydride; copper(II) sulfate; In N,N-dimethyl-formamide; mineral oil;

DOI:10.1002/chem.201002895

Reference yield:

(3S,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2,3,4-triol (168608-39-7) → (((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methoxy)(tert-butyl)diphenylsilane (168103-00-2)

Guidance literature:

Multi-step reaction with 2 steps

1: camphor-10-sulfonic acid; copper(II) sulfate / pH 2

2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 °C

With camphor-10-sulfonic acid; sodium hydride; copper(II) sulfate; In N,N-dimethyl-formamide; mineral oil;

DOI:10.1002/chem.201002895

upstream raw materials:

benzyl bromide

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

D-Arabinose

tert-butylchlorodiphenylsilane

Downstream raw materials:

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

5-azido-3-O-benzyl-5-deoxy-D-arabinono-1,4-lactone

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

dibenzyl 2-(((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl)malonate