(2S,3R,4S,5R)-5-hydroxy-6-(hydroxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyldiacetate

Base Information

• Chemical Name: (2S,3R,4S,5R)-5-hydroxy-6-(hydroxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyldiacetate
• CAS No.: 849834-73-7
• Molecular Formula: C₁₇H₂₂O₇S
• Molecular Weight: 370.423

Synonyms:(2S,3R,4S,5R)-5-hydroxy-6-(hydroxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyldiacetate

Chemical Property of (2S,3R,4S,5R)-5-hydroxy-6-(hydroxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyldiacetate

Chemical Property:

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Technology Process of (2S,3R,4S,5R)-5-hydroxy-6-(hydroxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyldiacetate

There total 11 articles about (2S,3R,4S,5R)-5-hydroxy-6-(hydroxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyldiacetate 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: 98.0%

1.3-propanedithiol (109-80-8) + 4-methylphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (219518-20-4) → (2S,3R,4S,5R)-5-hydroxy-6-(hydroxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyldiacetate (849834-73-7)

Guidance literature:

With vanadyl trifluoromethanesulfonate; In dichloromethane; acetonitrile; at 20 ℃; for 0.75h; Inert atmosphere;

DOI:10.1016/j.tet.2009.10.012

Reference yield: 93.0%

4-methylphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (219518-20-4) → (2S,3R,4S,5R)-5-hydroxy-6-(hydroxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyldiacetate (849834-73-7)

Guidance literature:

With acetic acid; In water; at 90 ℃; for 2.5h;

DOI:10.1016/j.tet.2005.01.015

Reference yield: 84.0%

4-methylphenyl 2,3-di-O-acetyl-4,6-O-(4-methoxybenzylidene)-β-D-thioglucopyranoside → (2S,3R,4S,5R)-5-hydroxy-6-(hydroxymethyl)-2-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyldiacetate (849834-73-7)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.joc.1c01907

upstream raw materials:

4-methylphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

1.3-propanedithiol

4-methylphenyl 2,3,4,6-tetrakis-O-trimethylsilyl-1-thio-β-D-glucopyranoside

4-methylphenyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside

Downstream raw materials:

4-methylphenyl 2,3-di-O-acetyl-4-azido-6-O-benzoyl-4-deoxy-1-thio-β-D-galactopyranoside

2-bromoethyl 4-azido-2,3,6-tri-O-benzoyl-4-deoxy-β-D-galactopyranoside

4-methylphenyl 4-azido-2,3,6-tri-O-benzoyl-4-deoxy-1-thio-β-D-galactopyranoside

4-methylphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

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