(2R,3R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-[(1'S,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-3-vinylcyclohexan-1-one

Base Information

Chemical Name:(2R,3R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-[(1'S,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-3-vinylcyclohexan-1-one
CAS No.:905312-40-5
Molecular Formula:C₃₀H₅₂O₅Si₂
Molecular Weight:548.911
Hs Code.:

Synonyms:(2R,3R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-[(1'S,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-3-vinylcyclohexan-1-one

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Chemical Property of (2R,3R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-[(1'S,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-3-vinylcyclohexan-1-one

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Technology Process of (2R,3R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-[(1'S,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-3-vinylcyclohexan-1-one

There total 4 articles about (2R,3R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-[(1'S,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-3-vinylcyclohexan-1-one 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: 51.0%

: 917-57-7
vinyllithium

: 109170-83-4
(S)-2-<(triethylsilyl)oxy>-2-propanal

: 581060-33-5
(4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-2-cyclohexenone

: 905312-40-5
(2R,3R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-[(1'S,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-3-vinylcyclohexan-1-one

: 905312-41-6
(2S,3R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-[(1'R,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-3-vinylcyclohexan-1-one

Guidance literature:: vinyllithium; With copper(l) cyanide; In diethyl ether; at -78 - 0 ℃;

(4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-2-cyclohexenone; In diethyl ether; at -78 ℃; for 0.5h;

(S)-2-<(triethylsilyl)oxy>-2-propanal; In diethyl ether; at -78 ℃; for 2h;
DOI:10.1016/j.tet.2006.04.079

Reference yield:

: 994-30-9
triethylsilyl chloride

: 905312-40-5
(2R,3R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-[(1'S,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-3-vinylcyclohexan-1-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 100 percent / imidazole / CH₂Cl₂ / 0.17 h / 0 - 20 °C

2.1: 70 percent / diisobutylaluminum hydride / toluene / 2 h / -78 °C

3.1: copper(I) cyanide / diethyl ether / -78 - 0 °C

3.2: diethyl ether / 0.5 h / -78 °C

3.3: 51 percent / diethyl ether / 2 h / -78 °C

With 1H-imidazole; copper(l) cyanide; diisobutylaluminium hydride; In diethyl ether; dichloromethane; toluene;
DOI:10.1016/j.tet.2006.04.079

Reference yield:

: 581060-36-8
(2S,4R)-2-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-hydroxy-cyclohexan-1-one

: 905312-40-5
(2R,3R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-[(1'S,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-3-vinylcyclohexan-1-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: MsCl; Et₃N / CH₂Cl₂ / 2.5 h / 0 °C

1.2: 3.50 g / HCl / H₂O

2.1: copper(I) cyanide / diethyl ether / -78 - 0 °C

2.2: diethyl ether / 0.5 h / -78 °C

2.3: 51 percent / diethyl ether / 2 h / -78 °C

With copper(l) cyanide; methanesulfonyl chloride; triethylamine; In diethyl ether; dichloromethane;
DOI:10.1016/j.tet.2006.04.079