(1R,3S,5S,6R,7S,8S,9S)-6,8-bis(benzyloxy)-9-<(tert-butyl)dimethylsilyloxy>-2,4,10-tri-oxatricyclo<3.3.1.1^3,7>decane

Base Information

• Chemical Name: (1R,3S,5S,6R,7S,8S,9S)-6,8-bis(benzyloxy)-9-<(tert-butyl)dimethylsilyloxy>-2,4,10-tri-oxatricyclo<3.3.1.1^3,7>decane
• CAS No.: 98510-24-8
• Molecular Formula: C₂₇H₃₆O₆Si
• Molecular Weight: 484.665

Synonyms:(1R,3S,5S,6R,7S,8S,9S)-6,8-bis(benzyloxy)-9-<(tert-butyl)dimethylsilyloxy>-2,4,10-tri-oxatricyclo<3.3.1.1^3,7>decane

Chemical Property of (1R,3S,5S,6R,7S,8S,9S)-6,8-bis(benzyloxy)-9-<(tert-butyl)dimethylsilyloxy>-2,4,10-tri-oxatricyclo<3.3.1.1^3,7>decane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (1R,3S,5S,6R,7S,8S,9S)-6,8-bis(benzyloxy)-9-<(tert-butyl)dimethylsilyloxy>-2,4,10-tri-oxatricyclo<3.3.1.1^3,7>decane

There total 3 articles about (1R,3S,5S,6R,7S,8S,9S)-6,8-bis(benzyloxy)-9-<(tert-butyl)dimethylsilyloxy>-2,4,10-tri-oxatricyclo<3.3.1.1^3,7>decane 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: 85.0%

benzyl bromide (100-39-0) + (1R,3S,5S,6R,7S,8S,9S)-9-<(tert-butyl)dimethylsilyloxy>-2,4,10-tri-oxatricyclo<3.3.1.13,7>decane-6,8-diol (98510-22-6) → (1R,3S,5S,6R,7S,8S,9S)-6,8-bis(benzyloxy)-9-<(tert-butyl)dimethylsilyloxy>-2,4,10-tri-oxatricyclo<3.3.1.13,7>decane (98510-24-8)

Guidance literature:

With sodium hydride; In tetrahydrofuran; paraffin; 1.) 0 deg C, 30 min, 2.) overnight;

DOI:10.1080/bbb.58.2046

Reference yield:

myo-Inositol orthoformate (98510-20-4) → (1R,3S,5S,6R,7S,8S,9S)-6,8-bis(benzyloxy)-9-<(tert-butyl)dimethylsilyloxy>-2,4,10-tri-oxatricyclo<3.3.1.13,7>decane (98510-24-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 48 percent / imidazole / dimethylformamide / 24 h / 0 - 20 °C

2: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, 24 h

With 1H-imidazole; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/jo00222a046

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (1R,3S,5S,6R,7S,8S,9S)-6,8-bis(benzyloxy)-9-<(tert-butyl)dimethylsilyloxy>-2,4,10-tri-oxatricyclo<3.3.1.13,7>decane (98510-24-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 48 percent / imidazole / dimethylformamide / 24 h / 0 - 20 °C

2: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, 24 h

With 1H-imidazole; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/jo00222a046

upstream raw materials:

benzyl bromide

(1R,3S,5S,6R,7S,8S,9S)-9-<(tert-butyl)dimethylsilyloxy>-2,4,10-tri-oxatricyclo<3.3.1.1^3,7>decane-6,8-diol

myo-Inositol orthoformate

tert-butyldimethylsilyl chloride

Downstream raw materials:

4,6-di-O-benzyl-myo-inositol

4,6-di-O-benzyl-2-O-tert-butyldimethylsilyl-1,3-O-methylene-myo-inositol

(1R,5R,6S,7S,8R,9S)-8,9-Bis-benzyloxy-2,4,10-trioxa-tricyclo[3.3.1.1^3,7]decan-6-ol

(1S,5S,7R,8S,9R)-8,9-Bis-benzyloxy-2,4,10-trioxa-tricyclo[3.3.1.1^3,7]decan-6-one

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