Methyl (1S,2R,3S,4R,5R)-5-<(tert-Butyl)dimethylsilyloxy>-3,4-dihydroxy-2-(phenylthio)cyclohexane-1-carboxylate

Base Information

Chemical Name:Methyl (1S,2R,3S,4R,5R)-5-<(tert-Butyl)dimethylsilyloxy>-3,4-dihydroxy-2-(phenylthio)cyclohexane-1-carboxylate
CAS No.:135711-55-6
Molecular Formula:C₂₀H₃₂O₆SSi
Molecular Weight:428.622
Hs Code.:

Synonyms:Methyl (1S,2R,3S,4R,5R)-5-<(tert-Butyl)dimethylsilyloxy>-3,4-dihydroxy-2-(phenylthio)cyclohexane-1-carboxylate

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Chemical Property of Methyl (1S,2R,3S,4R,5R)-5-<(tert-Butyl)dimethylsilyloxy>-3,4-dihydroxy-2-(phenylthio)cyclohexane-1-carboxylate

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Technology Process of Methyl (1S,2R,3S,4R,5R)-5-<(tert-Butyl)dimethylsilyloxy>-3,4-dihydroxy-2-(phenylthio)cyclohexane-1-carboxylate

There total 8 articles about Methyl (1S,2R,3S,4R,5R)-5-<(tert-Butyl)dimethylsilyloxy>-3,4-dihydroxy-2-(phenylthio)cyclohexane-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: 84.0%

: 135711-54-5
Methyl (1R,2S,3S,4S,5R)-5-<(tert-Butyl)dimethylsilyloxy>-1,2-epoxy-3,4-dihydroxycyclohexane-1-carboxylate

: 108-98-5
thiophenol

: 135711-57-8
(1S,2R,3S,4S,5R)-3-<(tert-Butyl)dimethylsilyloxy>-1,4-dihydroxy-2-(phenylthio)-6-oxabicyclo<3.2.1>octan-7-one

: 135711-56-7
(1S,2R,3S,4R,5R)-4-<(tert-Butyl)dimethylsilyloxy>-1,3-dihydroxy-2-(phenylthio)-6-oxabicyclo<3.2.1>octan-7-one

: 135711-55-6
Methyl (1S,2R,3S,4R,5R)-5-<(tert-Butyl)dimethylsilyloxy>-3,4-dihydroxy-2-(phenylthio)cyclohexane-1-carboxylate

Guidance literature:: With sodium thiophenolate; In dimethyl sulfoxide; for 20h; Ambient temperature;
DOI:10.1002/hlca.19910740415

Reference yield:

: 138-59-0
shikimic acid

: 135711-55-6
Methyl (1S,2R,3S,4R,5R)-5-<(tert-Butyl)dimethylsilyloxy>-3,4-dihydroxy-2-(phenylthio)cyclohexane-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: methanol; diethyl ether / -20 - -15 °C

2: 78 percent / Et₃N, 4-(dimethylamino)pyridine / dimethylformamide / 4 h / 0 °C

3: 87 percent / 3.0M t-BuOOH / VO(acac)2 / CH₂Cl₂; toluene / 18 h / Heating

4: 82 percent / Bu₄NF / tetrahydrofuran / 0.03 h

5: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature

With tert.-butylhydroperoxide; dmap; tetrabutyl ammonium fluoride; sodium thiophenolate; triethylamine; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1002/hlca.19910740415

Reference yield:

: 40983-58-2
methyl shikimate

: 135711-55-6
Methyl (1S,2R,3S,4R,5R)-5-<(tert-Butyl)dimethylsilyloxy>-3,4-dihydroxy-2-(phenylthio)cyclohexane-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 78 percent / Et₃N, 4-(dimethylamino)pyridine / dimethylformamide / 4 h / 0 °C

2: 87 percent / 3.0M t-BuOOH / VO(acac)2 / CH₂Cl₂; toluene / 18 h / Heating

3: 82 percent / Bu₄NF / tetrahydrofuran / 0.03 h

4: 84 percent / sodium thiophenolate / dimethylsulfoxide / 20 h / Ambient temperature

With tert.-butylhydroperoxide; dmap; tetrabutyl ammonium fluoride; sodium thiophenolate; triethylamine; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1002/hlca.19910740415