5-hydroxy-6-((4-methoxybenzyloxy)methyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl dibenzoate

Base Information

• Chemical Name: 5-hydroxy-6-((4-methoxybenzyloxy)methyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl dibenzoate
• CAS No.: 871095-80-6
• Molecular Formula: C₃₅H₃₄O₈S
• Molecular Weight: 614.716
• Mol file: 871095-80-6.mol

Synonyms:5-hydroxy-6-((4-methoxybenzyloxy)methyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl dibenzoate

Chemical Property of 5-hydroxy-6-((4-methoxybenzyloxy)methyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl dibenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-hydroxy-6-((4-methoxybenzyloxy)methyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl dibenzoate

There total 5 articles about 5-hydroxy-6-((4-methoxybenzyloxy)methyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl dibenzoate 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:

p-methylphenyl 1-thio-β-D-glucopyranoside (1152-39-2) → 5-hydroxy-6-((4-methoxybenzyloxy)methyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl dibenzoate (871095-80-6)

Guidance literature:

Multi-step reaction with 3 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

With dmap; camphor-10-sulfonic acid; sodium cyanoborohydride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja0484045

Reference yield:

4-methylphenyl (S)-4,6-O-[(4-methoxyphenyl)methylene]-1-thio-β-D-glucopyranoside (582322-04-1) → 5-hydroxy-6-((4-methoxybenzyloxy)methyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl dibenzoate (871095-80-6)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With dmap; sodium cyanoborohydride; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja0484045

Reference yield:

p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (28244-94-2,28244-99-7,86782-41-4,131488-65-8) → 5-hydroxy-6-((4-methoxybenzyloxy)methyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl dibenzoate (871095-80-6)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium methylate / dichloromethane; methanol / 1 h / 20 °C

2: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 6 h / 40 °C

3: pyridine / 0 - 20 °C

4: trifluoroacetic acid; sodium cyanoborohydride / N,N-dimethyl-formamide / 72 h / 0 - 20 °C / Molecular sieve

With pyridine; sodium methylate; sodium cyanoborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2016.07.042

upstream raw materials:

p-methylphenyl 1-thio-β-D-glucopyranoside

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

D-gulopyranose

β-D-glucose pentaacetate

Downstream raw materials:

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

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

p-methylphenyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranosyluronate)

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