(1R,2S,5R)-2-Allyl-1-benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-8-oxa-bicyclo[3.2.1]oct-6-en-3-one

Base Information

Chemical Name:(1R,2S,5R)-2-Allyl-1-benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-8-oxa-bicyclo[3.2.1]oct-6-en-3-one
CAS No.:349648-94-8
Molecular Formula:C₂₆H₃₈O₅Si
Molecular Weight:458.67
Hs Code.:

Synonyms:(1R,2S,5R)-2-Allyl-1-benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-8-oxa-bicyclo[3.2.1]oct-6-en-3-one

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Chemical Property of (1R,2S,5R)-2-Allyl-1-benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-8-oxa-bicyclo[3.2.1]oct-6-en-3-one

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Technology Process of (1R,2S,5R)-2-Allyl-1-benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-8-oxa-bicyclo[3.2.1]oct-6-en-3-one

There total 12 articles about (1R,2S,5R)-2-Allyl-1-benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-8-oxa-bicyclo[3.2.1]oct-6-en-3-one 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: 75.0%

: 349648-95-9
(1R,2R,5R)-2-Allyl-1-benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-8-oxa-bicyclo[3.2.1]oct-6-en-3-one

: 349648-94-8
(1R,2S,5R)-2-Allyl-1-benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-8-oxa-bicyclo[3.2.1]oct-6-en-3-one

Guidance literature:: With sodium methylate; In methanol;
DOI:10.1021/ja010643u

Reference yield: 70.0%

: 1826-67-1
vinyl magnesium bromide

: 349648-93-7
(1R,5R)-1-Benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-methylene-8-oxa-bicyclo[3.2.1]oct-6-en-3-one

: 349648-94-8
(1R,2S,5R)-2-Allyl-1-benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-8-oxa-bicyclo[3.2.1]oct-6-en-3-one

Guidance literature:: vinyl magnesium bromide; With copper(l) iodide; In diethyl ether; at -78 ℃; for 1h;

(1R,5R)-1-Benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-2-methylene-8-oxa-bicyclo[3.2.1]oct-6-en-3-one; In diethyl ether; at -78 ℃; for 0.5h; Further stages.;
DOI:10.1021/ja010643u

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 349648-94-8
(1R,2S,5R)-2-Allyl-1-benzyloxymethoxymethyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-8-oxa-bicyclo[3.2.1]oct-6-en-3-one

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / diisopropylethylamine / acetonitrile / 2 h / Heating

2: AIBN / benzene / 24 h / Heating

3: 75 percent / NaOMe / methanol

With sodium methylate; N-ethyl-N,N-diisopropylamine; 2,2'-azobis(isobutyronitrile); In methanol; acetonitrile; benzene;
DOI:10.1021/ja010643u