ethyl (1S,2S,4aR,6S,8S,8aS)-8-(tert-butyldimethylsiloxy)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6<<(p-toluenesulfonyl)oxy>methyl>naphthalene-1-carboxylate

Base Information

Chemical Name:ethyl (1S,2S,4aR,6S,8S,8aS)-8-(tert-butyldimethylsiloxy)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6<<(p-toluenesulfonyl)oxy>methyl>naphthalene-1-carboxylate
CAS No.:116097-25-7
Molecular Formula:C₂₈H₄₄O₆SSi
Molecular Weight:536.805
Hs Code.:

ethyl (1S,2S,4aR,6S,8S,8aS)-8-(tert-butyldimethylsiloxy)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6<<(p-toluenesulfonyl)oxy>methyl>naphthalene-1-carboxylate

Synonyms:ethyl (1S,2S,4aR,6S,8S,8aS)-8-(tert-butyldimethylsiloxy)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6<<(p-toluenesulfonyl)oxy>methyl>naphthalene-1-carboxylate

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Chemical Property of ethyl (1S,2S,4aR,6S,8S,8aS)-8-(tert-butyldimethylsiloxy)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6<<(p-toluenesulfonyl)oxy>methyl>naphthalene-1-carboxylate

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Technology Process of ethyl (1S,2S,4aR,6S,8S,8aS)-8-(tert-butyldimethylsiloxy)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6<<(p-toluenesulfonyl)oxy>methyl>naphthalene-1-carboxylate

There total 4 articles about ethyl (1S,2S,4aR,6S,8S,8aS)-8-(tert-butyldimethylsiloxy)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6<<(p-toluenesulfonyl)oxy>methyl>naphthalene-1-carboxylate 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: 95.0%

: 116097-24-6
ethyl (1S,2S,4aR,6S,8S,8aS)-8-(tert-butyldimethylsiloxy)-1,2,4a,5,6,7,8,8a-octahydro-6-(hydroxymethyl)-2-methylnaphthalene-1-carboxylate

: 98-59-9
p-toluenesulfonyl chloride

: 116097-25-7
ethyl (1S,2S,4aR,6S,8S,8aS)-8-(tert-butyldimethylsiloxy)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6<<(p-toluenesulfonyl)oxy>methyl>naphthalene-1-carboxylate

Guidance literature:: With pyridine; 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; In dichloromethane; for 90h;
DOI:10.1021/jo00047a011

Reference yield:

: 102299-03-6
(+)-ethyl (1S,2S,4aR,6S,8S,8aS)-6-(carboxymethyl)-1,2,4a,5,6,7,8,8a-octahydro-8-hydroxy-2-methylnaphthalene-1-carboxylate

: 116097-25-7
ethyl (1S,2S,4aR,6S,8S,8aS)-8-(tert-butyldimethylsiloxy)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6<<(p-toluenesulfonyl)oxy>methyl>naphthalene-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 1 h

2: 1.2 g / LiEt₃BH / tetrahydrofuran / 2 h / 0 °C

3: 95 percent / DMPA, pyridine / CH₂Cl₂ / 90 h

With pyridine; 2,6-dimethylpyridine; 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; lithium triethylborohydride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00047a011

Reference yield:

: 116135-23-0
ethyl (1S,2S,4aR,6S,8S,8aS)-8-(tert-butyldimethylsiloxy)-6-(carboxymethyl)-1,2,4a,5,6,7,8,8a-octahydro-2-methylnaphthalene-1-carboxylate

: 116097-25-7
ethyl (1S,2S,4aR,6S,8S,8aS)-8-(tert-butyldimethylsiloxy)-1,2,4a,5,6,7,8,8a-octahydro-2-methyl-6<<(p-toluenesulfonyl)oxy>methyl>naphthalene-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 1.2 g / LiEt₃BH / tetrahydrofuran / 2 h / 0 °C

2: 95 percent / DMPA, pyridine / CH₂Cl₂ / 90 h

With pyridine; 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; lithium triethylborohydride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00047a011