(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-4-vinylcyclohexan-2-ol

Base Information

Chemical Name:(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-4-vinylcyclohexan-2-ol
CAS No.:905312-43-8
Molecular Formula:C₃₀H₅₄O₅Si₂
Molecular Weight:550.927
Hs Code.:

Synonyms:(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-4-vinylcyclohexan-2-ol

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Chemical Property of (1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-4-vinylcyclohexan-2-ol

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Technology Process of (1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-4-vinylcyclohexan-2-ol

There total 7 articles about (1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-4-vinylcyclohexan-2-ol 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: 87.0%

: 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

: 905312-43-8
(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-4-vinylcyclohexan-2-ol

Guidance literature:: With lithium borohydride; acetic acid; In tetrahydrofuran; at 0 ℃; for 0.166667h;
DOI:10.1016/j.tet.2006.04.079

Reference yield:

: 905312-42-7
(4R,4aS,5R,6R,8S)-8-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2,4-bis-((S)-1-triethylsilanyloxy-ethyl)-5-vinyl-hexahydro-benzo[1,3]dioxin-8a-ol

: 905312-43-8
(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-4-vinylcyclohexan-2-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 76 percent / acetic acid / tetrahydrofuran / 72 h / 20 °C

2: 87 percent / acetic acid; LiBH₄ / tetrahydrofuran / 0.17 h / 0 °C

With lithium borohydride; acetic acid; In tetrahydrofuran;
DOI:10.1016/j.tet.2006.04.079

Reference yield:

: 994-30-9
triethylsilyl chloride

: 905312-43-8
(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-1'-hydroxy-2'-(triethylsilyloxy)propyl]-4-vinylcyclohexan-2-ol

Guidance literature:: Multi-step reaction with 4 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: 40 percent / diethyl ether / 2 h / -78 °C

4.1: 87 percent / acetic acid; LiBH₄ / tetrahydrofuran / 0.17 h / 0 °C

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