(5aS,6R,7R,9S,9aS)-9-benzyloxy-6-bromo-7-[(tert-butyldimethylsilyl)oxy]-6,7,8,9-tetrahydro-4-methoxy-9a(5aH)-dibenzofuranacetic acid ethyl ester

Base Information

Chemical Name:(5aS,6R,7R,9S,9aS)-9-benzyloxy-6-bromo-7-[(tert-butyldimethylsilyl)oxy]-6,7,8,9-tetrahydro-4-methoxy-9a(5aH)-dibenzofuranacetic acid ethyl ester
CAS No.:951396-68-2
Molecular Formula:C₃₀H₄₁BrO₆Si
Molecular Weight:605.641
Hs Code.:

(5aS,6R,7R,9S,9aS)-9-benzyloxy-6-bromo-7-[(tert-butyldimethylsilyl)oxy]-6,7,8,9-tetrahydro-4-methoxy-9a(5aH)-dibenzofuranacetic acid ethyl ester

Synonyms:(5aS,6R,7R,9S,9aS)-9-benzyloxy-6-bromo-7-[(tert-butyldimethylsilyl)oxy]-6,7,8,9-tetrahydro-4-methoxy-9a(5aH)-dibenzofuranacetic acid ethyl ester

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Chemical Property of (5aS,6R,7R,9S,9aS)-9-benzyloxy-6-bromo-7-[(tert-butyldimethylsilyl)oxy]-6,7,8,9-tetrahydro-4-methoxy-9a(5aH)-dibenzofuranacetic acid ethyl ester

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Technology Process of (5aS,6R,7R,9S,9aS)-9-benzyloxy-6-bromo-7-[(tert-butyldimethylsilyl)oxy]-6,7,8,9-tetrahydro-4-methoxy-9a(5aH)-dibenzofuranacetic acid ethyl ester

There total 5 articles about (5aS,6R,7R,9S,9aS)-9-benzyloxy-6-bromo-7-[(tert-butyldimethylsilyl)oxy]-6,7,8,9-tetrahydro-4-methoxy-9a(5aH)-dibenzofuranacetic acid ethyl ester 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: 84.0%

: 951396-64-8
(1S,4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-1-(2,3-dimethoxyphenyl)-2-cyclohexene-1-acetic acid ethyl ester

: 951396-68-2
(5aS,6R,7R,9S,9aS)-9-benzyloxy-6-bromo-7-[(tert-butyldimethylsilyl)oxy]-6,7,8,9-tetrahydro-4-methoxy-9a(5aH)-dibenzofuranacetic acid ethyl ester

Guidance literature:: With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 ℃;
DOI:10.1016/j.tetlet.2007.07.042

Reference yield:

: 951396-65-9
(1R,4S,6R)-4-benzyloxy-6-[(tert-butyldimethylsilyl)oxy]-3-(2,3-dimethoxyphenyl)-2-cyclohexen-1-ol

: 951396-68-2
(5aS,6R,7R,9S,9aS)-9-benzyloxy-6-bromo-7-[(tert-butyldimethylsilyl)oxy]-6,7,8,9-tetrahydro-4-methoxy-9a(5aH)-dibenzofuranacetic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / 2-nitrophenol / 60 h / 140 °C

2: 84 percent / NBS / dimethylformamide / 0 °C

With N-Bromosuccinimide; 2-hydroxynitrobenzene; In N,N-dimethyl-formamide; 1: Johnson-Claisen rearrangement;
DOI:10.1016/j.tetlet.2007.07.042

Reference yield:

: 951396-66-0
C₂₇H₃₈O₅Si

: 951396-68-2
(5aS,6R,7R,9S,9aS)-9-benzyloxy-6-bromo-7-[(tert-butyldimethylsilyl)oxy]-6,7,8,9-tetrahydro-4-methoxy-9a(5aH)-dibenzofuranacetic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 75 percent / PCC; NaOAc / 1,2-dichloro-ethane / 60 °C

2: 89 percent / NaBH₄; CeCl₃*7H₂O / methanol; CH₂Cl₂ / -78 °C

3: 80 percent / 2-nitrophenol / 60 h / 140 °C

4: 84 percent / NBS / dimethylformamide / 0 °C

With sodium tetrahydroborate; N-Bromosuccinimide; cerium(III) chloride; sodium acetate; pyridinium chlorochromate; 2-hydroxynitrobenzene; In methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 2: Luche reduction / 3: Johnson-Claisen rearrangement;
DOI:10.1016/j.tetlet.2007.07.042