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

Base Information

Chemical Name:[(2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl]-acetaldehyde
CAS No.:943858-57-9
Molecular Formula:C₂₂H₃₄O₅Si
Molecular Weight:406.594
Hs Code.:

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

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

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

There total 4 articles about [(2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl]-acetaldehyde 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: 89.0%

: 440333-69-7
2-[(2R,4aR,6S,7R,9aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl]-ethanol

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

Guidance literature:: With sulfur trioxide pyridine complex; triethylamine; In dichloromethane; dimethyl sulfoxide; at 0 ℃; for 1.5h;
DOI:10.1021/jo900332q

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

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

Guidance literature:: Multi-step reaction with 3 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

With 1H-imidazole; oxalyl dichloride; bis(cyclohexanyl)borane; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3.1: Swern oxidation;
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

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

Guidance literature:: Multi-step reaction with 3 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

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