(2S,3S,4R,5R,6S)-4,5-Bis-benzoyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-p-tolylsulfanyl-tetrahydro-pyran-2-carboxylic acid

Base Information

Chemical Name:(2S,3S,4R,5R,6S)-4,5-Bis-benzoyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-p-tolylsulfanyl-tetrahydro-pyran-2-carboxylic acid
CAS No.:871095-81-7
Molecular Formula:C₃₃H₃₈O₈SSi
Molecular Weight:622.811
Hs Code.:

Synonyms:(2S,3S,4R,5R,6S)-4,5-Bis-benzoyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-p-tolylsulfanyl-tetrahydro-pyran-2-carboxylic acid

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Chemical Property of (2S,3S,4R,5R,6S)-4,5-Bis-benzoyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-p-tolylsulfanyl-tetrahydro-pyran-2-carboxylic acid

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Technology Process of (2S,3S,4R,5R,6S)-4,5-Bis-benzoyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-p-tolylsulfanyl-tetrahydro-pyran-2-carboxylic acid

There total 9 articles about (2S,3S,4R,5R,6S)-4,5-Bis-benzoyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-p-tolylsulfanyl-tetrahydro-pyran-2-carboxylic acid 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:

: 727991-07-3
5-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyldibenzoate

: 871095-81-7
(2S,3S,4R,5R,6S)-4,5-Bis-benzoyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-p-tolylsulfanyl-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: With dipyridinium dichromate; In N,N-dimethyl-formamide; at 20 ℃; for 72h;
DOI:10.1021/ja0484045

Reference yield:

: 1152-39-2
p-methylphenyl 1-thio-β-D-glucopyranoside

: 871095-81-7
(2S,3S,4R,5R,6S)-4,5-Bis-benzoyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-p-tolylsulfanyl-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 70 percent / DL-10-camphorsulfonic acid / dimethylformamide; acetonitrile / 12 h / 20 °C

2: 86 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.42 h / 20 °C

3: NaBH₃CN; CF₃CO₂H / dimethylformamide / 0 - 20 °C

4: 13.2 g / Et₃N / CH₂Cl₂ / 3 h / 20 °C

5: 86 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 13 h / 20 °C

6: pyridinium dichromate / dimethylformamide / 72 h / 20 °C

With dmap; dipyridinium dichromate; camphor-10-sulfonic acid; sodium cyanoborohydride; triethylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja0484045

Reference yield:

: 582322-04-1
4-methylphenyl (S)-4,6-O-[(4-methoxyphenyl)methylene]-1-thio-β-D-glucopyranoside

: 871095-81-7
(2S,3S,4R,5R,6S)-4,5-Bis-benzoyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-p-tolylsulfanyl-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 86 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.42 h / 20 °C

2: NaBH₃CN; CF₃CO₂H / dimethylformamide / 0 - 20 °C

3: 13.2 g / Et₃N / CH₂Cl₂ / 3 h / 20 °C

4: 86 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 13 h / 20 °C

5: pyridinium dichromate / dimethylformamide / 72 h / 20 °C

With dmap; dipyridinium dichromate; sodium cyanoborohydride; triethylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja0484045