Toluene-4-sulfonic acid (1R,3S,4R,4aR,5S,6S,8R,8aR)-6-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-5-methoxymethoxy-3-methyl-octahydro-isochromen-4-yl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (1R,3S,4R,4aR,5S,6S,8R,8aR)-6-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-5-methoxymethoxy-3-methyl-octahydro-isochromen-4-yl ester
CAS No.:905312-47-2
Molecular Formula:C₃₂H₄₈O₉SSi
Molecular Weight:636.879
Hs Code.:

Toluene-4-sulfonic acid (1R,3S,4R,4aR,5S,6S,8R,8aR)-6-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-5-methoxymethoxy-3-methyl-octahydro-isochromen-4-yl ester

Synonyms:Toluene-4-sulfonic acid (1R,3S,4R,4aR,5S,6S,8R,8aR)-6-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-5-methoxymethoxy-3-methyl-octahydro-isochromen-4-yl ester

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Chemical Property of Toluene-4-sulfonic acid (1R,3S,4R,4aR,5S,6S,8R,8aR)-6-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-5-methoxymethoxy-3-methyl-octahydro-isochromen-4-yl ester

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Technology Process of Toluene-4-sulfonic acid (1R,3S,4R,4aR,5S,6S,8R,8aR)-6-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-5-methoxymethoxy-3-methyl-octahydro-isochromen-4-yl ester

There total 8 articles about Toluene-4-sulfonic acid (1R,3S,4R,4aR,5S,6S,8R,8aR)-6-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-5-methoxymethoxy-3-methyl-octahydro-isochromen-4-yl ester 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: 80.0%

: 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

: 905312-47-2
Toluene-4-sulfonic acid (1R,3S,4R,4aR,5S,6S,8R,8aR)-6-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-5-methoxymethoxy-3-methyl-octahydro-isochromen-4-yl ester

Guidance literature:: (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; With ozone; In methanol; at -78 ℃; for 0.1h;

With dimethylsulfide; In methanol; at -78 - 20 ℃; for 3h;
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

: 905312-47-2
Toluene-4-sulfonic acid (1R,3S,4R,4aR,5S,6S,8R,8aR)-6-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-5-methoxymethoxy-3-methyl-octahydro-isochromen-4-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C

2.1: 92 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 3.5 h / 50 °C

3.1: 86 percent / DDQ / acetonitrile; H₂O / 1 h / 0 - 20 °C

4.1: ozone / methanol / 0.1 h / -78 °C

4.2: 80 percent / Me₂S / methanol / 3 h / -78 - 20 °C

With n-butyllithium; ozone; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; 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

: 905312-47-2
Toluene-4-sulfonic acid (1R,3S,4R,4aR,5S,6S,8R,8aR)-6-benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-5-methoxymethoxy-3-methyl-octahydro-isochromen-4-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 92 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 3.5 h / 50 °C

2.1: 86 percent / DDQ / acetonitrile; H₂O / 1 h / 0 - 20 °C

3.1: ozone / methanol / 0.1 h / -78 °C

3.2: 80 percent / Me₂S / methanol / 3 h / -78 - 20 °C

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