(1S,3S,4R,6R,9R)-3-(tert-butyldiphenylsilanyloxy)-4,6-divinyl-5,10-dioxabicyclo[7.1.0]decane

Base Information

Chemical Name:(1S,3S,4R,6R,9R)-3-(tert-butyldiphenylsilanyloxy)-4,6-divinyl-5,10-dioxabicyclo[7.1.0]decane
CAS No.:852213-27-5
Molecular Formula:C₂₈H₃₆O₃Si
Molecular Weight:448.678
Hs Code.:

Synonyms:(1S,3S,4R,6R,9R)-3-(tert-butyldiphenylsilanyloxy)-4,6-divinyl-5,10-dioxabicyclo[7.1.0]decane

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Chemical Property of (1S,3S,4R,6R,9R)-3-(tert-butyldiphenylsilanyloxy)-4,6-divinyl-5,10-dioxabicyclo[7.1.0]decane

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Technology Process of (1S,3S,4R,6R,9R)-3-(tert-butyldiphenylsilanyloxy)-4,6-divinyl-5,10-dioxabicyclo[7.1.0]decane

There total 5 articles about (1S,3S,4R,6R,9R)-3-(tert-butyldiphenylsilanyloxy)-4,6-divinyl-5,10-dioxabicyclo[7.1.0]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: 98.0%

: 852213-26-4
(1S,3S,4R,6R,9R)-3-(tert-butyldiphenylsilanyloxy)-6-vinyl-5,10-dioxabicyclo[7.1.0]decane-4-carbaldehyde

: 1779-49-3
Methyltriphenylphosphonium bromide

: 852213-27-5
(1S,3S,4R,6R,9R)-3-(tert-butyldiphenylsilanyloxy)-4,6-divinyl-5,10-dioxabicyclo[7.1.0]decane

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.333333h;
DOI:10.1039/b413426e

Reference yield:

: 852213-25-3
(2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-hydroxymethyl-2-vinyl-2,3,4,7,8,9-hexahydrooxonine

: 852213-27-5
(1S,3S,4R,6R,9R)-3-(tert-butyldiphenylsilanyloxy)-4,6-divinyl-5,10-dioxabicyclo[7.1.0]decane

Guidance literature:: Multi-step reaction with 3 steps

1: 63 percent / mCPBA / tetrahydrofuran / 0 - 20 °C

2: 73 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 20 h / 20 °C

3: 98 percent / n-BuLi / tetrahydrofuran / 0.33 h / -78 °C

With n-butyllithium; 3-chloro-benzenecarboperoxoic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dimethyl sulfoxide; 3: Wittig methylenation;
DOI:10.1039/b413426e

Reference yield:

: 852213-31-1
(1S,3S,4R,6R,9S)-3-(tert-butyldiphenylsilanyloxy)-4-hydroxymethyl-6-vinyl-5,10-dioxabicyclo[7.1.0]decane

: 852213-27-5
(1S,3S,4R,6R,9R)-3-(tert-butyldiphenylsilanyloxy)-4,6-divinyl-5,10-dioxabicyclo[7.1.0]decane

Guidance literature:: Multi-step reaction with 2 steps

1: 73 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 20 h / 20 °C

2: 98 percent / n-BuLi / tetrahydrofuran / 0.33 h / -78 °C

With n-butyllithium; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dimethyl sulfoxide; 2: Wittig methylenation;
DOI:10.1039/b413426e