(1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-3-methyl-6-(3-((triisopropylsilyl)oxy)prop-1-en-2-yl)cyclohex-2-en-1-yl acrylate

Base Information

Chemical Name:(1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-3-methyl-6-(3-((triisopropylsilyl)oxy)prop-1-en-2-yl)cyclohex-2-en-1-yl acrylate
CAS No.:1404195-63-6
Molecular Formula:C₂₈H₅₂O₄Si₂
Molecular Weight:508.889
Hs Code.:

Synonyms:(1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-3-methyl-6-(3-((triisopropylsilyl)oxy)prop-1-en-2-yl)cyclohex-2-en-1-yl acrylate

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Chemical Property of (1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-3-methyl-6-(3-((triisopropylsilyl)oxy)prop-1-en-2-yl)cyclohex-2-en-1-yl acrylate

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Technology Process of (1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-3-methyl-6-(3-((triisopropylsilyl)oxy)prop-1-en-2-yl)cyclohex-2-en-1-yl acrylate

There total 7 articles about (1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-3-methyl-6-(3-((triisopropylsilyl)oxy)prop-1-en-2-yl)cyclohex-2-en-1-yl acrylate 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: 69.0%

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

: 814-68-6,25189-84-8
acryloyl chloride

: 1404195-63-6
(1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-3-methyl-6-(3-((triisopropylsilyl)oxy)prop-1-en-2-yl)cyclohex-2-en-1-yl acrylate

Guidance literature:: With pyridine; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;
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

: 1404195-63-6
(1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-3-methyl-6-(3-((triisopropylsilyl)oxy)prop-1-en-2-yl)cyclohex-2-en-1-yl acrylate

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: pyridine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; sodium tetrahydroborate; dipyridinium dichromate; L-Selectride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
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

: 1404195-63-6
(1R,4R,6R)-4-((tert-butyldimethylsilyl)oxy)-3-methyl-6-(3-((triisopropylsilyl)oxy)prop-1-en-2-yl)cyclohex-2-en-1-yl acrylate

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: pyridine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

With pyridine; dipyridinium dichromate; L-Selectride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol302570k DOI:10.1021/ol302570k