[(2R,4aR,6S,7R,9aS)-6-((Z)-But-2-enyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy]-tert-butyl-dimethyl-silane

Base Information

Chemical Name:[(2R,4aR,6S,7R,9aS)-6-((Z)-But-2-enyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy]-tert-butyl-dimethyl-silane
CAS No.:440334-01-0
Molecular Formula:C₂₄H₃₈O₄Si
Molecular Weight:418.649
Hs Code.:

Synonyms:[(2R,4aR,6S,7R,9aS)-6-((Z)-But-2-enyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy]-tert-butyl-dimethyl-silane

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Chemical Property of [(2R,4aR,6S,7R,9aS)-6-((Z)-But-2-enyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy]-tert-butyl-dimethyl-silane

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Technology Process of [(2R,4aR,6S,7R,9aS)-6-((Z)-But-2-enyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy]-tert-butyl-dimethyl-silane

There total 5 articles about [(2R,4aR,6S,7R,9aS)-6-((Z)-But-2-enyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy]-tert-butyl-dimethyl-silane 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: 33.0%

: 1530-32-1
ethyltriphenylphosphonium bromide

: 943858-57-9
[(2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl]-acetaldehyde

: 440334-01-0
[(2R,4aR,6S,7R,9aS)-6-((Z)-But-2-enyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy]-tert-butyl-dimethyl-silane

Guidance literature:: ethyltriphenylphosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃;

[(2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl]-acetaldehyde; In tetrahydrofuran;
DOI:10.1016/S0040-4020(02)00039-X

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 440334-01-0
[(2R,4aR,6S,7R,9aS)-6-((Z)-But-2-enyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 96 percent / imidazole / dimethylformamide / 50 °C

2.1: (c-Hex)2BH / tetrahydrofuran / 0 °C

2.2: 99 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran

3.1: DMSO; (COCl)2 / CH₂Cl₂ / -78 °C

3.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: NaHMDS / tetrahydrofuran / 0 °C

4.2: 33 percent / tetrahydrofuran

With 1H-imidazole; oxalyl dichloride; bis(cyclohexanyl)borane; sodium hexamethyldisilazane; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3.1: Swern oxidation / 4.2: Wittig reaction;
DOI:10.1016/S0040-4020(02)00039-X

Reference yield:

: 213815-32-8
(2R,4aR,6S,7R,9aS)-2-Phenyl-6-vinyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

: 440334-01-0
[(2R,4aR,6S,7R,9aS)-6-((Z)-But-2-enyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 96 percent / imidazole / dimethylformamide / 50 °C

2.1: (c-Hex)2BH / tetrahydrofuran / 0 °C

2.2: 99 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran

3.1: DMSO; (COCl)2 / CH₂Cl₂ / -78 °C

3.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: NaHMDS / tetrahydrofuran / 0 °C

4.2: 33 percent / tetrahydrofuran

With 1H-imidazole; oxalyl dichloride; bis(cyclohexanyl)borane; sodium hexamethyldisilazane; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3.1: Swern oxidation / 4.2: Wittig reaction;
DOI:10.1016/S0040-4020(02)00039-X