Methyl 2,3-dibenzoyl-4,6-O-benzylidene-beta-D-galactopyranoside

Base Information

• Chemical Name: Methyl 2,3-dibenzoyl-4,6-O-benzylidene-beta-D-galactopyranoside
• CAS No.: 53598-03-1
• Molecular Formula: C28H26 O8
• Molecular Weight: 490.5
• Nikkaji Number: J2.312.193J
• Mol file: 53598-03-1.mol

Synonyms:53598-03-1;METHYL 2,3-DIBENZOYL-4,6-O-BENZYLIDENE-BETA-D-GALACTOPYRANOSIDE;Methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-b-D-galactopyranoside;[(4Ar,6R,7R,8S,8aS)-7-benzoyloxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] benzoate;W-203017;Methyl 2,3-Dibenzoyl-4,6-O-benzylidene-?-D-galactopyranoside

Chemical Property of Methyl 2,3-dibenzoyl-4,6-O-benzylidene-beta-D-galactopyranoside

Chemical Property:

• PSA: 89.52000
• LogP: 3.92310
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 490.16276778
• Heavy Atom Count: 36
• Complexity: 725

Purity/Quality:

95% ^*data from raw suppliers

Methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-b-D-galactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C2C(O1)COC(O2)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5
• Isomeric SMILES: CO[C@H]1[C@@H]([C@H]([C@@H]2[C@H](O1)COC(O2)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5
• Uses: A useful synthetic intermediate. METHYL 2,3-DIBENZOYL-4,6-O-BENZYLIDENE-BETA-D-GALACTOPYRANOSIDE is a useful synthetic intermediate.

Technology Process of Methyl 2,3-dibenzoyl-4,6-O-benzylidene-beta-D-galactopyranoside

There total 21 articles about Methyl 2,3-dibenzoyl-4,6-O-benzylidene-beta-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: 98.0%

benzoyl chloride (98-88-4) + 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside (6748-85-2,6748-91-0,6884-04-4,6953-72-6,53598-03-1,56253-30-6,56253-32-8,80244-97-9,86420-74-8,109718-79-8,120200-46-6,120200-51-3,120201-28-7,120292-61-7)

Guidance literature:

With pyridine; In dichloromethane; Ambient temperature;

DOI:10.1071/CH9900665

Reference yield: 95.0%

methyl 4,6-O-benzylidene-α-D-glucopyranoside (3162-96-7) + benzoyl chloride (98-88-4) → methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside (6748-85-2,6748-91-0,6884-04-4,6953-72-6,53598-03-1,56253-30-6,56253-32-8,80244-97-9,86420-74-8,109718-79-8,120200-46-6,120200-51-3,120201-28-7,120292-61-7)

Guidance literature:

With pyridine; Ambient temperature;

Reference yield: 93.0%

benzaldehyde dimethyl acetal (1125-88-8) + methyl 2,3-di-O-benzoyl-α-D-glucopyranoside (4137-35-3,23397-67-3,102518-21-8,109681-62-1,117124-69-3,149035-49-4) → methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside (6748-85-2,6748-91-0,6884-04-4,6953-72-6,53598-03-1,56253-30-6,56253-32-8,80244-97-9,86420-74-8,109718-79-8,120200-46-6,120200-51-3,120201-28-7,120292-61-7)

Guidance literature:

With 1,3,5-trichloro-2,4,6-triazine; In acetonitrile; at 60 ℃; for 0.166667h; regioselective reaction; Sonication; Inert atmosphere;

DOI:10.1039/c2ob25452b

upstream raw materials:

benzoyl chloride

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside

methyl 4,6-O-benzylidene-α-D-glucopyranoside

D-Glucose

Downstream raw materials:

methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside

methyl 2,3,4-tri-O-benzoylglucopyranoside

methyl 2,3-di-O-benzoyl-4-O-benzyl-α-D-glucopyranoside

methyl 2,3-di-O-benzoyl-α-D-glucopyranoside

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