(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-2-methoxymethyloxy-4-vinylcyclohexane

Base Information

Chemical Name:(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-2-methoxymethyloxy-4-vinylcyclohexane
CAS No.:905312-46-1
Molecular Formula:C₃₃H₅₀O₈SSi
Molecular Weight:634.907
Hs Code.:

(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-2-methoxymethyloxy-4-vinylcyclohexane

Synonyms:(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-2-methoxymethyloxy-4-vinylcyclohexane

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Chemical Property of (1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-2-methoxymethyloxy-4-vinylcyclohexane

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Technology Process of (1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-2-methoxymethyloxy-4-vinylcyclohexane

There total 7 articles about (1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-2-methoxymethyloxy-4-vinylcyclohexane 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: 86.0%

: 905312-45-0
(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-1'-(p-toluenesulfonyloxy)-2'-(triethylsilyloxy)propyl]-2-methoxymethyloxy-4-vinylcyclohexane

: 905312-46-1
(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-2-methoxymethyloxy-4-vinylcyclohexane

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In water; acetonitrile; at 0 - 20 ℃; for 1h;
DOI:10.1016/j.tet.2006.04.079

Reference yield:

: 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

: 905312-46-1
(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-2-methoxymethyloxy-4-vinylcyclohexane

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C

2: 92 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 3.5 h / 50 °C

3: 86 percent / DDQ / acetonitrile; H₂O / 1 h / 0 - 20 °C

With n-butyllithium; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; water; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1016/j.tet.2006.04.079

Reference yield:

: 905312-44-9
(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-1'-(p-toluenesulfonyloxy)-2'-(triethylsilyloxy)propyl]-4-vinylcyclohexan-2-ol

: 905312-46-1
(1S,2S,3S,4R,5R)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-[(1'R,2'S)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-2-methoxymethyloxy-4-vinylcyclohexane

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 3.5 h / 50 °C

2: 86 percent / DDQ / acetonitrile; H₂O / 1 h / 0 - 20 °C

With N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In water; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1016/j.tet.2006.04.079