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

Base Information

Chemical Name:5-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyldibenzoate
CAS No.:727991-07-3
Molecular Formula:C₃₃H₄₀O₇SSi
Molecular Weight:608.828
Hs Code.:

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

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Chemical Property of 5-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyldibenzoate

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Technology Process of 5-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyldibenzoate

There total 8 articles about 5-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyldibenzoate 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: 96.0%

: 727991-06-2
5-(tert-butyldimethylsilyloxy)-6-((4-methoxybenzyloxy)methyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyldibenzoate

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

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃;
DOI:10.1016/j.tet.2016.07.042

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

With dmap; 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

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

Guidance literature:: Multi-step reaction with 4 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

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