(1S,4S,6R)-4-[(tert-butyldimethylsilyl)oxy]-6-methyl-2-vinyl-2-cyclohexen-1-yl-isobutyrate

Base Information

Chemical Name:(1S,4S,6R)-4-[(tert-butyldimethylsilyl)oxy]-6-methyl-2-vinyl-2-cyclohexen-1-yl-isobutyrate
CAS No.:473536-51-5
Molecular Formula:C₁₉H₃₄O₃Si
Molecular Weight:338.563
Hs Code.:

Synonyms:(1S,4S,6R)-4-[(tert-butyldimethylsilyl)oxy]-6-methyl-2-vinyl-2-cyclohexen-1-yl-isobutyrate

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Chemical Property of (1S,4S,6R)-4-[(tert-butyldimethylsilyl)oxy]-6-methyl-2-vinyl-2-cyclohexen-1-yl-isobutyrate

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Technology Process of (1S,4S,6R)-4-[(tert-butyldimethylsilyl)oxy]-6-methyl-2-vinyl-2-cyclohexen-1-yl-isobutyrate

There total 12 articles about (1S,4S,6R)-4-[(tert-butyldimethylsilyl)oxy]-6-methyl-2-vinyl-2-cyclohexen-1-yl-isobutyrate 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: 78.0%

: 7486-35-3
tri-n-butyl(vinyl)tin

: 473536-60-6
Isobutyric acid (1S,4S,6R)-2-bromo-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-cyclohex-2-enyl ester

: 473536-51-5
(1S,4S,6R)-4-[(tert-butyldimethylsilyl)oxy]-6-methyl-2-vinyl-2-cyclohexen-1-yl-isobutyrate

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 90 ℃; for 24h;
DOI:10.1002/1521-3773(20020802)41:15<2755::AID-ANIE2755>3.0.CO;2-A

Reference yield: 78.0%

: (4S,6R)-2-bromo-4-[(tert-butyldimethylsilyl)oxy]-6-methyl-2-cyclohexen-1-yl isobutyrate

: 7486-35-3
tri-n-butyl(vinyl)tin

: 473536-51-5
(1S,4S,6R)-4-[(tert-butyldimethylsilyl)oxy]-6-methyl-2-vinyl-2-cyclohexen-1-yl-isobutyrate

Guidance literature:: tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 90 ℃; for 24h;
DOI:10.1002/chem.200600809

Reference yield:

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

: 473536-51-5
(1S,4S,6R)-4-[(tert-butyldimethylsilyl)oxy]-6-methyl-2-vinyl-2-cyclohexen-1-yl-isobutyrate

Guidance literature:: Multi-step reaction with 4 steps

1.1: bromine / CCl₄ / 0 °C

1.2: 80 percent / triethylamine / CCl₄ / 32 h / 20 °C

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

3.1: 158 mg / 4-dimethylaminopyridine / CH₂Cl₂ / 1 h

4.1: 78 percent / tetrakistriphenylphosphine palladium / toluene / 24 h / 90 °C

With dmap; lithium aluminium tetrahydride; bromine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; tetrachloromethane; dichloromethane; toluene; 4.1: Stille coupling;
DOI:10.1002/chem.200600809