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

Base Information

Chemical Name:(1S,3S,4R,6R,9R)-3-(tert-butyldiphenylsilanyloxy)-6-vinyl-5,10-dioxabicyclo[7.1.0]decane-4-carbaldehyde
CAS No.:852213-26-4
Molecular Formula:C₂₇H₃₄O₄Si
Molecular Weight:450.65
Hs Code.:

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

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

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

There total 4 articles about (1S,3S,4R,6R,9R)-3-(tert-butyldiphenylsilanyloxy)-6-vinyl-5,10-dioxabicyclo[7.1.0]decane-4-carbaldehyde 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: 73.0%

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

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

Guidance literature:: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 20 ℃; for 20h;
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

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

Guidance literature:: Multi-step reaction with 2 steps

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

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

With 3-chloro-benzenecarboperoxoic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dimethyl sulfoxide;
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

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

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 73 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 20 h / 20 °C

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