(4R,6R)-4-(tert-butyldimethylsilyloxy)-3-methyl-6-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-2-enone

Base Information

Chemical Name:(4R,6R)-4-(tert-butyldimethylsilyloxy)-3-methyl-6-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-2-enone
CAS No.:1404195-62-5
Molecular Formula:C₂₅H₄₈O₃Si₂
Molecular Weight:452.825
Hs Code.:

Synonyms:(4R,6R)-4-(tert-butyldimethylsilyloxy)-3-methyl-6-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-2-enone

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Chemical Property of (4R,6R)-4-(tert-butyldimethylsilyloxy)-3-methyl-6-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-2-enone

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Technology Process of (4R,6R)-4-(tert-butyldimethylsilyloxy)-3-methyl-6-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-2-enone

There total 5 articles about (4R,6R)-4-(tert-butyldimethylsilyloxy)-3-methyl-6-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-2-enone 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: 71.0%

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

: 1404195-62-5
(4R,6R)-4-(tert-butyldimethylsilyloxy)-3-methyl-6-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-2-enone

Guidance literature:: With dipyridinium dichromate; In dichloromethane; at 50 ℃; for 12h; Inert atmosphere;
DOI:10.1021/ol302570k DOI:10.1021/ol302570k

Reference yield:

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

: 1404195-62-5
(4R,6R)-4-(tert-butyldimethylsilyloxy)-3-methyl-6-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-2-enone

Guidance literature:: Multi-step reaction with 2 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 15 h / 0 - 20 °C / Inert atmosphere

2: dipyridinium dichromate / dichloromethane / 12 h / 50 °C / Inert atmosphere

With 1H-imidazole; dipyridinium dichromate; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol302570k DOI:10.1021/ol302570k

Reference yield:

: 1404195-48-7
(R)-2-methyl-5-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-2-enone

: 1404195-62-5
(4R,6R)-4-(tert-butyldimethylsilyloxy)-3-methyl-6-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-2-enone

Guidance literature:: Multi-step reaction with 5 steps

1.1: methylmagnesium bromide; iron(III) chloride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

1.2: 15 h / 20 °C / Inert atmosphere

2.1: 3-chloro-benzenecarboperoxoic acid; sodium hydrogencarbonate / dichloromethane / 2 h / -78 °C / Inert atmosphere

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

4.1: 1H-imidazole / N,N-dimethyl-formamide / 15 h / 0 - 20 °C / Inert atmosphere

5.1: dipyridinium dichromate / dichloromethane / 12 h / 50 °C / Inert atmosphere

With 1H-imidazole; iron(III) chloride; sodium tetrahydroborate; dipyridinium dichromate; methylmagnesium bromide; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol302570k DOI:10.1021/ol302570k