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

Base Information

Chemical Name:(1S,4S,6R)-6-(tert-butyldimethylsilyloxy)-1-methyl-4-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-2-enol
CAS No.:1404195-51-2
Molecular Formula:C₂₅H₅₀O₃Si₂
Molecular Weight:454.841
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 4 articles about (1S,4S,6R)-6-(tert-butyldimethylsilyloxy)-1-methyl-4-(3-(triisopropylsilyloxy)prop-1-en-2-yl)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: 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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 steps

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

2: 1H-imidazole / N,N-dimethyl-formamide / 15 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/ol302570k DOI:10.1021/ol302570k