1-((1S,2R,5R)-5-((tert-butyldimethylsilyl)oxy)-2-hydroxy-4-methylcyclohex-3-en-1-yl)-2-((triisopropylsilyl)oxy)ethanone

Base Information

Chemical Name:1-((1S,2R,5R)-5-((tert-butyldimethylsilyl)oxy)-2-hydroxy-4-methylcyclohex-3-en-1-yl)-2-((triisopropylsilyl)oxy)ethanone
CAS No.:1404195-54-5
Molecular Formula:C₂₄H₄₈O₄Si₂
Molecular Weight:456.814
Hs Code.:

Synonyms:1-((1S,2R,5R)-5-((tert-butyldimethylsilyl)oxy)-2-hydroxy-4-methylcyclohex-3-en-1-yl)-2-((triisopropylsilyl)oxy)ethanone

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Chemical Property of 1-((1S,2R,5R)-5-((tert-butyldimethylsilyl)oxy)-2-hydroxy-4-methylcyclohex-3-en-1-yl)-2-((triisopropylsilyl)oxy)ethanone

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Technology Process of 1-((1S,2R,5R)-5-((tert-butyldimethylsilyl)oxy)-2-hydroxy-4-methylcyclohex-3-en-1-yl)-2-((triisopropylsilyl)oxy)ethanone

There total 6 articles about 1-((1S,2R,5R)-5-((tert-butyldimethylsilyl)oxy)-2-hydroxy-4-methylcyclohex-3-en-1-yl)-2-((triisopropylsilyl)oxy)ethanone 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: 45.0%

: 1404195-52-3
(1R,4R,6R)-4-(tert-butyldimethylsilyloxy)-3-methyl-6-(3-(triisopropylsilyloxy)prop-1-en-2-yl)cyclohex-2-enol

: 1404195-54-5
1-((1S,2R,5R)-5-((tert-butyldimethylsilyl)oxy)-2-hydroxy-4-methylcyclohex-3-en-1-yl)-2-((triisopropylsilyl)oxy)ethanone

Guidance literature:: With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; In 1,4-dioxane; water; tert-butyl alcohol; for 6h;
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

: 1404195-54-5
1-((1S,2R,5R)-5-((tert-butyldimethylsilyl)oxy)-2-hydroxy-4-methylcyclohex-3-en-1-yl)-2-((triisopropylsilyl)oxy)ethanone

Guidance literature:: Multi-step reaction with 5 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

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

4: L-Selectride / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

5: sodium periodate; osmium(VIII) oxide; 2,6-dimethylpyridine / water; 1,4-dioxane; tert-butyl alcohol / 6 h

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; dipyridinium dichromate; L-Selectride; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ol302570k DOI:10.1021/ol302570k

Reference yield:

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

: 1404195-54-5
1-((1S,2R,5R)-5-((tert-butyldimethylsilyl)oxy)-2-hydroxy-4-methylcyclohex-3-en-1-yl)-2-((triisopropylsilyl)oxy)ethanone

Guidance literature:: Multi-step reaction with 3 steps

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

2: L-Selectride / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

3: sodium periodate; osmium(VIII) oxide; 2,6-dimethylpyridine / water; 1,4-dioxane; tert-butyl alcohol / 6 h

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; dipyridinium dichromate; L-Selectride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/ol302570k DOI:10.1021/ol302570k