(1R,2S,5S)-2-methyl-5-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-3-ene-1,2-diol

Base Information

Chemical Name:(1R,2S,5S)-2-methyl-5-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-3-ene-1,2-diol
CAS No.:1404195-61-4
Molecular Formula:C₁₉H₃₆O₃Si
Molecular Weight:340.579
Hs Code.:

Synonyms:(1R,2S,5S)-2-methyl-5-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-3-ene-1,2-diol

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Chemical Property of (1R,2S,5S)-2-methyl-5-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-3-ene-1,2-diol

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Technology Process of (1R,2S,5S)-2-methyl-5-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-3-ene-1,2-diol

There total 2 articles about (1R,2S,5S)-2-methyl-5-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-3-ene-1,2-diol 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: 65.0%

: 1404195-50-1
(2S,5S)-2-hydroxy-2-methyl-5-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-3-enone

: 1404195-61-4
(1R,2S,5S)-2-methyl-5-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-3-ene-1,2-diol

Guidance literature:: With sodium tetrahydroborate; In methanol; at -78 ℃; for 1.5h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ol302570k DOI:10.1021/ol302570k

Reference yield:

: 1404195-49-8
(S)-triisopropyl(2-(4-methyl-5-(trimethylsilyloxy)cyclohexa-2,4-dienyl)allyloxy)silane

: 1404195-61-4
(1R,2S,5S)-2-methyl-5-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-3-ene-1,2-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 3-chloro-benzenecarboperoxoic acid; sodium hydrogencarbonate / dichloromethane / 2 h / -78 °C / Inert atmosphere

2: sodium tetrahydroborate / methanol / 1.5 h / -78 °C / Inert atmosphere

With sodium tetrahydroborate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;
DOI:10.1021/ol302570k DOI:10.1021/ol302570k

Reference yield: 95.0%

: 1404195-61-4
(1R,2S,5S)-2-methyl-5-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-3-ene-1,2-diol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1404195-51-2
(1S,4S,6R)-6-(tert-butyldimethylsilyloxy)-1-methyl-4-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-2-enol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 15h; Inert atmosphere;
DOI:10.1021/ol302570k DOI:10.1021/ol302570k