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

Base Information

• Chemical Name: (1R,5S,6S,7R,8S,9R)-6,8-Bis-benzyloxy-9-benzyloxymethoxy-2,4,10-trioxa-tricyclo[3.3.1.1^3,7]decane
• CAS No.: 115133-07-8
• Molecular Formula: C₂₉H₃₀O₇
• Molecular Weight: 490.553

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

Chemical Property of (1R,5S,6S,7R,8S,9R)-6,8-Bis-benzyloxy-9-benzyloxymethoxy-2,4,10-trioxa-tricyclo[3.3.1.1^3,7]decane

Chemical Property:

Purity/Quality:

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Technology Process of (1R,5S,6S,7R,8S,9R)-6,8-Bis-benzyloxy-9-benzyloxymethoxy-2,4,10-trioxa-tricyclo[3.3.1.1^3,7]decane

There total 2 articles about (1R,5S,6S,7R,8S,9R)-6,8-Bis-benzyloxy-9-benzyloxymethoxy-2,4,10-trioxa-tricyclo[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:

Benzyloxymethyl chloride (3587-60-8) → (1R,5S,6S,7R,8S,9R)-6,8-Bis-benzyloxy-9-benzyloxymethoxy-2,4,10-trioxa-tricyclo[3.3.1.13,7]decane (115133-07-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DMF, rt, 30 min, 2.) rt, 3 h

2: 1.) NaH / 1.) DMF, rt, 30 min, 2.) rt, 3 h

With sodium hydride;

DOI:10.1016/S0040-4039(00)96548-1

Reference yield:

benzyl bromide (100-39-0) + 4-O-benzyloxymethyl-myo-inosytol 1,3,5-orthoformate (115133-06-7,135556-68-2) → (1R,5S,6S,7R,8S,9R)-6,8-Bis-benzyloxy-9-benzyloxymethoxy-2,4,10-trioxa-tricyclo[3.3.1.13,7]decane (115133-07-8)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) DMF, rt, 30 min, 2.) rt, 3 h;

DOI:10.1016/S0040-4039(00)96548-1

Reference yield: 66.0%

(1R,5S,6S,7R,8S,9R)-6,8-Bis-benzyloxy-9-benzyloxymethoxy-2,4,10-trioxa-tricyclo[3.3.1.13,7]decane (115133-07-8) → racemic 2,4-di-O-benzyl-myo-inositol (16749-97-6,114419-12-4,115015-97-9,115184-74-2,118354-56-6,130404-34-1,149713-85-9,1214834-30-6)

Guidance literature:

With hydrogenchloride; In 1,2-dimethoxyethane; for 18h; Ambient temperature;

DOI:10.1016/S0040-4039(00)96548-1

upstream raw materials:

benzyl bromide

4-O-benzyloxymethyl-myo-inosytol 1,3,5-orthoformate

Benzyloxymethyl chloride

Downstream raw materials:

racemic 2,4-di-O-benzyl-myo-inositol

myo-inositol 1,3,4,5-tetrakisphosphate

(+/-) 2,6-di-O-benzyl-myo-inositol 1,3,4,5-tetrakis(dibenzylphosphate)

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