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

Base Information

Chemical Name:(1S,3S,4R,6R,9S)-3-(tert-butyldiphenylsilanyloxy)-4-hydroxymethyl-6-vinyl-5,10-dioxabicyclo[7.1.0]decane
CAS No.:852213-31-1
Molecular Formula:C₂₇H₃₆O₄Si
Molecular Weight:452.666
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 3 articles about (1S,3S,4R,6R,9S)-3-(tert-butyldiphenylsilanyloxy)-4-hydroxymethyl-6-vinyl-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: 63.0%

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

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

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

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1039/b413426e

Reference yield:

: 852213-23-1
(2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2-vinyl-2,3,4,7,8,9-hexahydrooxonine

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

Guidance literature:: Multi-step reaction with 2 steps

1: 89 percent / HF*py; pyridine / tetrahydrofuran / 16 h

2: 63 percent / mCPBA / tetrahydrofuran / 0 - 20 °C

With pyridine; pyridine hydrogenfluoride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran;
DOI:10.1039/b413426e

Reference yield:

: 749924-31-0
(2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2,3,4,7,8,9-hexahydrooxonine-2-carbaldehyde

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

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / n-BuLi / tetrahydrofuran / 0.33 h / -78 °C

2: 89 percent / HF*py; pyridine / tetrahydrofuran / 16 h

3: 63 percent / mCPBA / tetrahydrofuran / 0 - 20 °C

With pyridine; n-butyllithium; pyridine hydrogenfluoride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1: Wittig methylenation;
DOI:10.1039/b413426e