(2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-2,9-divinyl-2,3,4,7,8,9-hexahydrooxonine

Base Information

Chemical Name:(2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-2,9-divinyl-2,3,4,7,8,9-hexahydrooxonine
CAS No.:852213-20-8
Molecular Formula:C₂₈H₃₆O₂Si
Molecular Weight:432.678
Hs Code.:

Synonyms:(2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-2,9-divinyl-2,3,4,7,8,9-hexahydrooxonine

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Chemical Property of (2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-2,9-divinyl-2,3,4,7,8,9-hexahydrooxonine

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Technology Process of (2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-2,9-divinyl-2,3,4,7,8,9-hexahydrooxonine

There total 4 articles about (2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-2,9-divinyl-2,3,4,7,8,9-hexahydrooxonine 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: 93.0%

: 852213-30-0
(2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-2-vinyl-2,3,4,7,8,9-hexahydrooxonine-9-carbaldehyde

: 1779-49-3
Methyltriphenylphosphonium bromide

: 852213-20-8
(2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-2,9-divinyl-2,3,4,7,8,9-hexahydrooxonine

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;
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

: 852213-20-8
(2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-2,9-divinyl-2,3,4,7,8,9-hexahydrooxonine

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 16 h / 20 °C

2: 93 percent / n-BuLi / tetrahydrofuran / 1 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

Reference yield:

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

: 852213-20-8
(2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-2,9-divinyl-2,3,4,7,8,9-hexahydrooxonine

Guidance literature:: Multi-step reaction with 3 steps

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

2: 94 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 16 h / 20 °C

3: 93 percent / n-BuLi / tetrahydrofuran / 1 h / -78 °C

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