(2R,3R)-2-[(1R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-3-methyl-pent-4-en-1-ol

Base Information

• Chemical Name: (2R,3R)-2-[(1R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-3-methyl-pent-4-en-1-ol
• CAS No.: 108712-52-3
• Molecular Formula: C₁₈H₃₄O₂Si
• Molecular Weight: 310.552

Synonyms:(2R,3R)-2-[(1R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-3-methyl-pent-4-en-1-ol

Chemical Property of (2R,3R)-2-[(1R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-3-methyl-pent-4-en-1-ol

Chemical Property:

Purity/Quality:

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Technology Process of (2R,3R)-2-[(1R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-3-methyl-pent-4-en-1-ol

There total 8 articles about (2R,3R)-2-[(1R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-3-methyl-pent-4-en-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: 78.0%

2,2-Dimethyl-propionic acid (R)-2-[(1R,6R)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-3-methyl-pent-4-enyl ester (108712-51-2) → (2R,3R)-2-[(1R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-3-methyl-pent-4-en-1-ol (108712-52-3) + (2R,3S)-2-[(1R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-3-methyl-pent-4-en-1-ol (108712-52-3,108813-28-1)

Guidance literature:

With methyllithium; In diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1021/jo00392a009

Reference yield: 78.0%

2,2-Dimethyl-propionic acid (R)-2-[(1R,6R)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-3-methyl-pent-4-enyl ester (108712-51-2) → (2R,3R)-2-[(1R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-3-methyl-pent-4-en-1-ol (108712-52-3) + (2R,3S)-2-[(1R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-3-methyl-pent-4-en-1-ol (108712-52-3,108813-28-1)

Guidance literature:

With methyllithium; In diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1021/jo00392a009

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (2R,3R)-2-[(1R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-3-methyl-pent-4-en-1-ol (108712-52-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / Ambient temperature

2: 78 percent / methyllithium / diethyl ether / 0.5 h / 0 °C

With 2,6-dimethylpyridine; methyllithium; In diethyl ether; dichloromethane;

DOI:10.1021/jo00392a009

upstream raw materials:

2,2-Dimethyl-propionic acid (R)-2-[(1R,6R)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-3-methyl-pent-4-enyl ester

t-butyldimethylsiyl triflate

2,2-Dimethyl-propionic acid (R)-2-((1R,6R)-6-hydroxy-cyclohex-2-enyl)-3-methyl-pent-4-enyl ester

(1S,2S)-2-((S)-1-Hydroxymethyl-2-methyl-but-3-enyl)-cyclohex-3-enol

Downstream raw materials:

<1α,2α(1R^*,2R^*)>-(+/-)-(1,1-dimethylethyl)dimethyl<<2-<2-methyl-1-<(phenylthio)methyl>-3-butenyl>-3-cyclohexen-1-yl>oxy>silane

(2S,4R,6R)-2-{(3S,4S)-2-Benzenesulfonyl-3-[(1S,6S)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-4-methyl-hex-5-enyl}-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran

(2S,4R,6R)-2-{(3R,4R)-2-Benzenesulfonyl-3-[(1R,6R)-6-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-4-methyl-hex-5-enyl}-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran

(3S,4S)-4-[(1S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-6-[(2R,4R,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-3-methyl-hexanal

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