(1S,4S,6R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-cyclohex-2-enol

Base Information

Chemical Name:(1S,4S,6R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-cyclohex-2-enol
CAS No.:473536-59-3
Molecular Formula:C₁₃H₂₅BrO₂Si
Molecular Weight:321.33
Hs Code.:

Synonyms:(1S,4S,6R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-cyclohex-2-enol

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Chemical Property of (1S,4S,6R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-cyclohex-2-enol

Chemical Property:

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Technology Process of (1S,4S,6R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-cyclohex-2-enol

There total 6 articles about (1S,4S,6R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-cyclohex-2-enol 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:

: (4S,6R)-2,3-Dibromo-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-cyclohexanone

: 473536-59-3
(1S,4S,6R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-cyclohex-2-enol

: (1R,4S,6R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-cyclohex-2-enol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at -100 ℃; for 0.5h;
DOI:10.1002/1521-3773(20020802)41:15<2755::AID-ANIE2755>3.0.CO;2-A

Reference yield:

: 473536-57-1
(4S,6R)-4-[(tert-butyldimethylsilyl)oxy]-6-methyl-2-cyclohexen-1-one

: 473536-59-3
(1S,4S,6R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-cyclohex-2-enol

Guidance literature:: Multi-step reaction with 2 steps

1: Br₂ / CCl₄ / 0 °C

2: LiAlH₄ / tetrahydrofuran / 0.5 h / -100 °C

With lithium aluminium tetrahydride; bromine; In tetrahydrofuran; tetrachloromethane;
DOI:10.1002/1521-3773(20020802)41:15<2755::AID-ANIE2755>3.0.CO;2-A

Reference yield:

: 473536-54-8
(4R,5R)-4-hydroxy-5-methyl-4-[(p-tolylsulfonyl)methyl]-2-cyclohexen-1-one

: 473536-59-3
(1S,4S,6R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-cyclohex-2-enol

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / DIBAL-H / tetrahydrofuran / 0.5 h / -78 °C

2: 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

3: Cs₂CO₃ / acetonitrile / 17 h / 0 °C

4: Br₂ / CCl₄ / 0 °C

5: LiAlH₄ / tetrahydrofuran / 0.5 h / -100 °C

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; bromine; diisobutylaluminium hydride; caesium carbonate; In tetrahydrofuran; tetrachloromethane; dichloromethane; acetonitrile;
DOI:10.1002/1521-3773(20020802)41:15<2755::AID-ANIE2755>3.0.CO;2-A