(1S,2S,5R)-2-i-propyl-5-methyl-1-(3-t-butyldimethylsiloxy-1-propyn-1-yl)cyclohexan-1-ol

Base Information

Chemical Name:(1S,2S,5R)-2-i-propyl-5-methyl-1-(3-t-butyldimethylsiloxy-1-propyn-1-yl)cyclohexan-1-ol
CAS No.:306973-69-3
Molecular Formula:C₁₉H₃₆O₂Si
Molecular Weight:324.579
Hs Code.:

Synonyms:(1S,2S,5R)-2-i-propyl-5-methyl-1-(3-t-butyldimethylsiloxy-1-propyn-1-yl)cyclohexan-1-ol

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Chemical Property of (1S,2S,5R)-2-i-propyl-5-methyl-1-(3-t-butyldimethylsiloxy-1-propyn-1-yl)cyclohexan-1-ol

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Technology Process of (1S,2S,5R)-2-i-propyl-5-methyl-1-(3-t-butyldimethylsiloxy-1-propyn-1-yl)cyclohexan-1-ol

There total 1 articles about (1S,2S,5R)-2-i-propyl-5-methyl-1-(3-t-butyldimethylsiloxy-1-propyn-1-yl)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: 83.0%

: 10458-14-7,14073-97-3,17627-49-5,7786-64-3
(2R,5S)-menthone

: 76782-82-6
tert-Butyldimethyl(prop-2-ynyloxy)silane

: 306973-69-3
(1S,2S,5R)-2-i-propyl-5-methyl-1-(3-t-butyldimethylsiloxy-1-propyn-1-yl)cyclohexan-1-ol

: (1R,2S,5R)-2-i-propyl-5-methyl-1-(3-t-butyldimethylsiloxy-1-propyn-1-yl)cyclohexan-1-ol

Guidance literature:: tert-Butyldimethyl(prop-2-ynyloxy)silane; With n-butyllithium; cerium(III) chloride; In tetrahydrofuran; at -78 ℃; for 1h;

(2R,5S)-menthone; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1021/jo000810t

Reference yield: 73.0%

: 306973-69-3
(1S,2S,5R)-2-i-propyl-5-methyl-1-(3-t-butyldimethylsiloxy-1-propyn-1-yl)cyclohexan-1-ol

: 750594-48-0
(1R,2S,5R)-2-i-propyl-5-methyl-1-(3-t-butyldimethylsyloxy-1-propen-1-yl)cyclohexan-1-ol

Guidance literature:: With sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; at 0 ℃; for 14h;
DOI:10.1021/jo000810t

Reference yield:

: 306973-69-3
(1S,2S,5R)-2-i-propyl-5-methyl-1-(3-t-butyldimethylsiloxy-1-propyn-1-yl)cyclohexan-1-ol

: (R)-3-(t-butyldimethylsiloxy)-2-(dimethylphenylsilyl)propan-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 73 percent / Red-Al / tetrahydrofuran / 14 h / 0 °C

2.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C

2.2: tetrahydrofuran / 3.5 h / -78 - 20 °C

3.1: CuI; LiI / tetrahydrofuran / 0.5 h / -30 °C

3.2: 59 percent / tetrahydrofuran / 14 h / 20 °C

4.1: O₃ / CH₂Cl₂ / -78 °C

4.2: sodium borohydride / methanol / 10 h / 20 °C

With copper(l) iodide; n-butyllithium; ozone; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium iodide; In tetrahydrofuran; dichloromethane; 1.1: Reduction / 2.1: Metallation / 2.2: Etherification / 3.1: Metallation / 3.2: Addition / 4.1: Ozonolysis / 4.2: Ring cleavage;
DOI:10.1021/jo000810t