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

Base Information

Chemical Name:(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'R)-1'-hydroxy-2'-(4-methoxybenzyloxy)propyl]-4-vinylcyclohexan-2-ol
CAS No.:581060-38-0
Molecular Formula:C₃₂H₄₈O₆Si
Molecular Weight:556.815
Hs Code.:

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

There total 13 articles about (1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'R)-1'-hydroxy-2'-(4-methoxybenzyloxy)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: 70.0%

: 581060-32-4
(2S,3R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-[(1'R,2'R)-1'-hydroxy-2'-(4-methoxybenzyloxy)propyl]-3-vinylcyclohexan-1-one

: 581060-38-0
(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'R)-1'-hydroxy-2'-(4-methoxybenzyloxy)propyl]-4-vinylcyclohexan-2-ol

Guidance literature:: With tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; acetic acid;
DOI:10.1016/S0040-4039(03)01186-9

Reference yield:

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

: 581060-38-0
(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'R)-1'-hydroxy-2'-(4-methoxybenzyloxy)propyl]-4-vinylcyclohexan-2-ol

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: diethyl ether / 0.5 h / -78 °C

1.3: 85 percent / diethyl ether / 0.33 h / -78 °C

2.1: 70 percent / Me₄NBH(OAc)3; acetic acid / tetrahydrofuran / 24 h / 0 - 20 °C

With copper(l) cyanide; acetic acid; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether;
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

: 581060-38-0
(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'R)-1'-hydroxy-2'-(4-methoxybenzyloxy)propyl]-4-vinylcyclohexan-2-ol

Guidance literature:: Multi-step reaction with 3 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: 85 percent / diethyl ether / 0.33 h / -78 °C

3.1: 70 percent / Me₄NBH(OAc)3; acetic acid / tetrahydrofuran / 24 h / 0 - 20 °C

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