(2R,4aR,6S,7R,9aS)-6-((Z)-But-2-enyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

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Chemical Name:(2R,4aR,6S,7R,9aS)-6-((Z)-But-2-enyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol
CAS No.:440333-60-8
Molecular Formula:C₁₈H₂₄O₄
Molecular Weight:304.386
Hs Code.:

Synonyms:(2R,4aR,6S,7R,9aS)-6-((Z)-But-2-enyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

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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-ol

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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-ol

There total 5 articles about (2R,4aR,6S,7R,9aS)-6-((Z)-But-2-enyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol 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: 99.0%

: 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

: 440333-60-8
(2R,4aR,6S,7R,9aS)-6-((Z)-But-2-enyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;
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

: 440333-60-8
(2R,4aR,6S,7R,9aS)-6-((Z)-But-2-enyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

Guidance literature:: Multi-step reaction with 5 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

5.1: 99 percent / TBAF / tetrahydrofuran / 20 °C

With 1H-imidazole; oxalyl dichloride; bis(cyclohexanyl)borane; tetrabutyl ammonium fluoride; 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:

: 440334-00-9
tert-Butyl-dimethyl-((2R,4aR,6S,7R,9aS)-2-phenyl-6-vinyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-yloxy)-silane

: 440333-60-8
(2R,4aR,6S,7R,9aS)-6-((Z)-But-2-enyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: 99 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran

2.1: DMSO; (COCl)2 / CH₂Cl₂ / -78 °C

2.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: NaHMDS / tetrahydrofuran / 0 °C

3.2: 33 percent / tetrahydrofuran

4.1: 99 percent / TBAF / tetrahydrofuran / 20 °C

With oxalyl dichloride; bis(cyclohexanyl)borane; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 2.1: Swern oxidation / 3.2: Wittig reaction;
DOI:10.1016/S0040-4020(02)00039-X