(1S,2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-1-vinyl-cyclohexan-1-ol

Base Information

Chemical Name:(1S,2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-1-vinyl-cyclohexan-1-ol
CAS No.:946524-49-8
Molecular Formula:C₂₈H₅₆O₂Si₂
Molecular Weight:480.922
Hs Code.:

Synonyms:(1S,2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-1-vinyl-cyclohexan-1-ol

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Chemical Property of (1S,2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-1-vinyl-cyclohexan-1-ol

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Technology Process of (1S,2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-1-vinyl-cyclohexan-1-ol

There total 6 articles about (1S,2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-1-vinyl-cyclohexan-1-ol 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: 93.0%

: 946524-57-8
C₂₈H₅₄O₂Si₂

: 946524-49-8
(1S,2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-1-vinyl-cyclohexan-1-ol

Guidance literature:: With pyridine; hydrogen; palladium on barium sulfate; In methanol; for 18h;
DOI:10.1021/ol070992e

Reference yield: 87.0%

: 946524-47-6
(2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-cyclohexan-1-one

: 1826-67-1
vinyl magnesium bromide

: 946524-49-8
(1S,2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-1-vinyl-cyclohexan-1-ol

Guidance literature:: vinyl magnesium bromide; With cerium(III) chloride; In tetrahydrofuran; at -78 ℃;

(2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-cyclohexan-1-one; In tetrahydrofuran; at -78 - -15 ℃; Further stages.;
DOI:10.1021/ol070992e

Reference yield:

: 166317-79-9
(2S,5R)-5-methyl-2-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-cyclohexan-1-one

: 946524-49-8
(1S,2S,3R,6S)-3-methyl-6-((R)-1-methyl-2-triisopropylsilanyloxy-ethyl)-2-((E)-3-methylsilanyl-but-2-enyl)-1-vinyl-cyclohexan-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: LDA / tetrahydrofuran / -78 - 0 °C

1.2: hexamethylphosphoric triamide / tetrahydrofuran / 0.08 h / -78 °C

1.3: 89 percent / diethyl zinc / tetrahydrofuran / -78 - 20 °C

2.1: n-BuLi / tetrahydrofuran / -78 - 0 °C

2.2: tetrahydrofuran / -78 - 20 °C

3.1: 0.316 g / potassium carbonate; MeOH

4.1: 93 percent / hydrogen; pyridine / Pd on BaSO₄ / methanol / 18 h

With pyridine; methanol; n-butyllithium; hydrogen; potassium carbonate; lithium diisopropyl amide; palladium on barium sulfate; In tetrahydrofuran; methanol;
DOI:10.1021/ol070992e