5-Phenyl-2-thioxo-1-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-1,2-dihydro-pyrrole-3,3-dicarboxylic acid diethyl ester

Base Information

• Chemical Name: 5-Phenyl-2-thioxo-1-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-1,2-dihydro-pyrrole-3,3-dicarboxylic acid diethyl ester
• CAS No.: 213838-35-8
• Molecular Formula: C₃₀H₃₅NO₁₃S
• Molecular Weight: 649.673

Synonyms:

Chemical Property of 5-Phenyl-2-thioxo-1-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-1,2-dihydro-pyrrole-3,3-dicarboxylic acid diethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 5-Phenyl-2-thioxo-1-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-1,2-dihydro-pyrrole-3,3-dicarboxylic acid diethyl ester

There total 4 articles about 5-Phenyl-2-thioxo-1-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-1,2-dihydro-pyrrole-3,3-dicarboxylic acid diethyl ester 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: 76.0%

N-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2,2-diethoxycarbonyl-4-phenyl-4-oxothiobutanamide (213838-31-4) → 5-Phenyl-2-thioxo-1-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-1,2-dihydro-pyrrole-3,3-dicarboxylic acid diethyl ester (213838-35-8)

Guidance literature:

With phosphoric acid; acetic anhydride; for 12h; Ambient temperature;

DOI:10.1016/S0957-4166(98)00243-2

Reference yield:

diethyl phenacylmalonate (94011-49-1) → 5-Phenyl-2-thioxo-1-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-1,2-dihydro-pyrrole-3,3-dicarboxylic acid diethyl ester (213838-35-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DMF, 5 min, 2.) DMF, 30 deg C

2: 76 percent / H₃PO₄, Ac₂O / 12 h / Ambient temperature

With phosphoric acid; acetic anhydride; sodium hydride;

DOI:10.1016/S0957-4166(98)00243-2

Reference yield:

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (14152-97-7) → 5-Phenyl-2-thioxo-1-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-1,2-dihydro-pyrrole-3,3-dicarboxylic acid diethyl ester (213838-35-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DMF, 5 min, 2.) DMF, 30 deg C

2: 76 percent / H₃PO₄, Ac₂O / 12 h / Ambient temperature

With phosphoric acid; acetic anhydride; sodium hydride;

DOI:10.1016/S0957-4166(98)00243-2

upstream raw materials:

N-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2,2-diethoxycarbonyl-4-phenyl-4-oxothiobutanamide

diethyl phenacylmalonate

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate

diethyl malonate

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