(1R,5S)-3-(2-(triisopropylsilyloxy)ethyl)-2-methyl-5-(prop-1-en-2-yl)-1-(prop-2-ynyl)cyclohex-2-enol

Base Information

Chemical Name:(1R,5S)-3-(2-(triisopropylsilyloxy)ethyl)-2-methyl-5-(prop-1-en-2-yl)-1-(prop-2-ynyl)cyclohex-2-enol
CAS No.:1359761-49-1
Molecular Formula:C₂₄H₄₂O₂Si
Molecular Weight:390.682
Hs Code.:

Synonyms:(1R,5S)-3-(2-(triisopropylsilyloxy)ethyl)-2-methyl-5-(prop-1-en-2-yl)-1-(prop-2-ynyl)cyclohex-2-enol

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Chemical Property of (1R,5S)-3-(2-(triisopropylsilyloxy)ethyl)-2-methyl-5-(prop-1-en-2-yl)-1-(prop-2-ynyl)cyclohex-2-enol

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Technology Process of (1R,5S)-3-(2-(triisopropylsilyloxy)ethyl)-2-methyl-5-(prop-1-en-2-yl)-1-(prop-2-ynyl)cyclohex-2-enol

There total 5 articles about (1R,5S)-3-(2-(triisopropylsilyloxy)ethyl)-2-methyl-5-(prop-1-en-2-yl)-1-(prop-2-ynyl)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: 88.0%

: 1359761-48-0
(S)-3-(2-triisopropylsilyloxyethyl)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

: 106-96-7
propargyl bromide

: 1359761-49-1
(1R,5S)-3-(2-(triisopropylsilyloxy)ethyl)-2-methyl-5-(prop-1-en-2-yl)-1-(prop-2-ynyl)cyclohex-2-enol

Guidance literature:: With iodine; magnesium; mercury dichloride; In diethyl ether; toluene; at 20 ℃; for 20h; Inert atmosphere;
DOI:10.1021/ol300058t

Reference yield:

: 1359761-47-9
(1S,5R)-1-(2-triisopropylsilyloxyethyl)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enol

: 1359761-49-1
(1R,5S)-3-(2-(triisopropylsilyloxy)ethyl)-2-methyl-5-(prop-1-en-2-yl)-1-(prop-2-ynyl)cyclohex-2-enol

Guidance literature:: Multi-step reaction with 2 steps

1: pyridinium chlorochromate / dichloromethane / 54 h / 23 °C

2: iodine; magnesium; mercury dichloride / diethyl ether; toluene / 20 h / 20 °C / Inert atmosphere

With iodine; magnesium; pyridinium chlorochromate; mercury dichloride; In diethyl ether; dichloromethane; toluene;
DOI:10.1021/ol300058t

Reference yield:

: 6485-40-1,2244-16-8
(R)-Carvone

: 1359761-49-1
(1R,5S)-3-(2-(triisopropylsilyloxy)ethyl)-2-methyl-5-(prop-1-en-2-yl)-1-(prop-2-ynyl)cyclohex-2-enol

Guidance literature:: Multi-step reaction with 5 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 1.17 h / -78 °C

1.2: 2 h / -78 °C

2.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 20 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 14 h / 20 °C

4.1: pyridinium chlorochromate / dichloromethane / 54 h / 23 °C

5.1: iodine; magnesium; mercury dichloride / diethyl ether; toluene / 20 h / 20 °C / Inert atmosphere

With 1H-imidazole; lithium aluminium tetrahydride; iodine; magnesium; pyridinium chlorochromate; mercury dichloride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol300058t