(2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl diacetate

Base Information

• Chemical Name: (2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl diacetate
• CAS No.: 84635-42-7
• Molecular Formula: C₂₁H₂₇NO₈S
• Molecular Weight: 453.513

Synonyms:(2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl diacetate

Chemical Property of (2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl diacetate

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

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Technology Process of (2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl diacetate

There total 10 articles about (2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl diacetate 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: 97.0%

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranose (51450-09-0) + 4-tolyl iodide (624-31-7) → (2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl diacetate (84635-42-7)

Guidance literature:

With C₅₁H₄₂NOP₂Pd⁽¹⁺⁾*CH₃O₃S^(1-); triethylamine; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/chem.201501050

Reference yield: 92.0%

para-thiocresol (106-45-6) + 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3) → (2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl diacetate (84635-42-7)

Guidance literature:

With molybdenum(VI) oxychloride; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tet.2010.12.024

Reference yield: 89.0%

para-thiocresol (106-45-6) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → (2R,3S,4R,5R,6S)-5-acetamido-2-(acetoxymethyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4-diyl diacetate (84635-42-7)

Guidance literature:

With potassium carbonate; for 1h; Neat (no solvent); Ball milling;

DOI:10.1039/b904454j

upstream raw materials:

para-thiocresol

Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester

2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

Downstream raw materials:

2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline

4-methylphenyl 2-acetamido-2-deoxy-1-thio-β-D-glucopyranoside

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