(5α,6β)-2-bromo-5-hydroxy-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>cyclohexa-1,3-diene

Base Information

Chemical Name:(5α,6β)-2-bromo-5-hydroxy-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>cyclohexa-1,3-diene
CAS No.:121073-20-9
Molecular Formula:C₁₂H₂₁BrO₂Si
Molecular Weight:305.287
Hs Code.:

Synonyms:(5α,6β)-2-bromo-5-hydroxy-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>cyclohexa-1,3-diene

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Chemical Property of (5α,6β)-2-bromo-5-hydroxy-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>cyclohexa-1,3-diene

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Technology Process of (5α,6β)-2-bromo-5-hydroxy-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>cyclohexa-1,3-diene

There total 6 articles about (5α,6β)-2-bromo-5-hydroxy-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>cyclohexa-1,3-diene 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: 67.0%

: 121073-18-5
(3β,4α,5β)-1-bromo-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-hydroxy-5-(phenylseleno)cyclohex-1-ene

: 121073-20-9
(5α,6β)-2-bromo-5-hydroxy-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>cyclohexa-1,3-diene

Guidance literature:: With tetrabutylammonium periodite; sodium phosphate; In chloroform; for 14h; Ambient temperature;
DOI:10.1021/jo00273a005

Reference yield:

: 121073-14-1
1-bromo-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>cyclohexa-1,4-diene

: 121073-20-9
(5α,6β)-2-bromo-5-hydroxy-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>cyclohexa-1,3-diene

Guidance literature:: Multi-step reaction with 3 steps

1: 44 percent / sodium phosphate, m-CPBA / CHCl₃ / 43 h / Ambient temperature

2: 30 percent / NaBH₄ / methanol / 1.) 0 deg C, 12 h, 2.) RT, 24 h

3: 67 percent / sodium phosphate, tetrabutylammonium periodate / CHCl₃ / 14 h / Ambient temperature

With sodium tetrahydroborate; tetrabutylammonium periodite; 3-chloro-benzenecarboperoxoic acid; sodium phosphate; In methanol; chloroform;
DOI:10.1021/jo00273a005

Reference yield:

: 121073-10-7
(3β,4β)-1-bromo-3-hydroxy-4-(phenylseleno)cyclohex-1-ene

: 121073-20-9
(5α,6β)-2-bromo-5-hydroxy-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>cyclohexa-1,3-diene

Guidance literature:: Multi-step reaction with 5 steps

1: Et₃N, DMAP / CH₂Cl₂ / 50 h / Heating

2: sodium phosphate, tetrabutylammonium periodate / CHCl₃ / 24 h

3: 44 percent / sodium phosphate, m-CPBA / CHCl₃ / 43 h / Ambient temperature

4: 30 percent / NaBH₄ / methanol / 1.) 0 deg C, 12 h, 2.) RT, 24 h

5: 67 percent / sodium phosphate, tetrabutylammonium periodate / CHCl₃ / 14 h / Ambient temperature

With dmap; sodium tetrahydroborate; tetrabutylammonium periodite; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium phosphate; In methanol; dichloromethane; chloroform;
DOI:10.1021/jo00273a005