p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-levulinyl-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-levulinyl-1-thio-β-D-galactopyranoside
• CAS No.: 258333-94-7
• Molecular Formula: C₃₂H₃₂O₈S
• Molecular Weight: 576.667

Synonyms:p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-levulinyl-1-thio-β-D-galactopyranoside

Chemical Property of p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-levulinyl-1-thio-β-D-galactopyranoside

Chemical Property:

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Technology Process of p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-levulinyl-1-thio-β-D-galactopyranoside

There total 12 articles about p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-levulinyl-1-thio-β-D-galactopyranoside 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: 85.0%

levulinic acid (123-76-2) + p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (220645-55-6) → p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-levulinyl-1-thio-β-D-galactopyranoside (258333-94-7)

Guidance literature:

With dmap; diisopropyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 3h;

DOI:10.1021/acs.joc.6b02745

Reference yield: 82.0%

p-tolyl 3-O-levulinoyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside (895567-71-2) + benzoyl chloride (98-88-4) → p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-levulinyl-1-thio-β-D-galactopyranoside (258333-94-7)

Guidance literature:

With dmap; In dichloromethane; at 50 ℃; Inert atmosphere;

DOI:10.1002/anie.201205601

Reference yield:

p-methylphenyl-1-thio-β-D-galactopyranoside (1152-39-2,28244-98-6,121523-95-3,131488-68-1) → p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-levulinyl-1-thio-β-D-galactopyranoside (258333-94-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / camphorsulfonic acid / acetonitrile / 2 h / Ambient temperature

2: 1.) DCC, DMAP, 2.) pyridine / 1.) CH₂Cl₂, RT, 3 h, 2.) reflux

With pyridine; dmap; camphor-10-sulfonic acid; dicyclohexyl-carbodiimide; In acetonitrile;

DOI:10.1021/ja982232s

upstream raw materials:

benzoyl chloride

levulinic acid

p-methylphenyl 4,6-O-benzylidene-1-thio-β-D-galactopyranoside

p-methylphenyl-1-thio-β-D-galactopyranoside

Downstream raw materials:

p-tolyl 2,3-di-O-levulinoyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1→3)-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

N-fluorenylmethyloxycarbonyl-O-[2-O-benzoyl-3-O-levulinoyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1→4)-2,3-di-O-benzoyl-β-D-xylopyranosyl]-L-serine benzyl ester

p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

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