(1R,4S,5R,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-yloxy tert-butyldimethylsilane

Base Information

Chemical Name:(1R,4S,5R,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-yloxy tert-butyldimethylsilane
CAS No.:1283695-54-4
Molecular Formula:C₂₀H₃₀O₄Si
Molecular Weight:362.541
Hs Code.:

Synonyms:(1R,4S,5R,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-yloxy tert-butyldimethylsilane

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Chemical Property of (1R,4S,5R,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-yloxy tert-butyldimethylsilane

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Technology Process of (1R,4S,5R,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-yloxy tert-butyldimethylsilane

There total 4 articles about (1R,4S,5R,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-yloxy tert-butyldimethylsilane 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: 94.0%

: 1283695-41-9
(1R,4S,5R,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-ol

: 1283695-54-4
(1R,4S,5R,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-yloxy tert-butyldimethylsilane

Guidance literature:: With 1H-imidazole; dmap; tert-butyldimethylsilyl chloride; In dichloromethane; at 0 - 20 ℃; for 1h; Inert atmosphere;
DOI:10.1002/anie.201007327

Reference yield:

: 1283695-39-5
(1S,2R,5S,7R)-7-(benzyloxymethyl)-2-phenylthio-6,8-dioxabicyclo[3.2.1]oct-3-ene

: 1283695-54-4
(1R,4S,5R,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-yloxy tert-butyldimethylsilane

Guidance literature:: Multi-step reaction with 2 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.5 h / -78 °C / Inert atmosphere

1.2: 6 h / -78 °C / Inert atmosphere; Reflux

2.1: 1H-imidazole; dmap; tert-butyldimethylsilyl chloride / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; dmap; tert-butyldimethylsilyl chloride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;
DOI:10.1002/anie.201007327

Reference yield:

: (1S,5S,7R)-7-Benzyloxymethyl-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-one

: 1283695-54-4
(1R,4S,5R,7R)-7-(benzyloxymethyl)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-yloxy tert-butyldimethylsilane

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 1 h / 0 - 20 °C / Inert atmosphere

2.1: pyridine; tributylphosphine / 16 h / 0 - 60 °C / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.5 h / -78 °C / Inert atmosphere

3.2: 6 h / -78 °C / Inert atmosphere; Reflux

4.1: 1H-imidazole; dmap; tert-butyldimethylsilyl chloride / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; tributylphosphine; cerium(III) chloride heptahydrate; tert-butyldimethylsilyl chloride; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; 2.1: Hata reaction;
DOI:10.1002/anie.201007327