Methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-b-D-glucopyranoside

Base Information

• Chemical Name: Methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-b-D-glucopyranoside
• CAS No.: 56253-32-8
• Molecular Formula: C28H26 O8
• Molecular Weight: 490.51
• DSSTox Substance ID: DTXSID20474244
• Mol file: 56253-32-8.mol

Synonyms:56253-32-8;Methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-b-D-glucopyranoside;[(4aR,6R,7R,8S,8aR)-7-benzoyloxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] benzoate;SCHEMBL7148505;DTXSID20474244;W-203123

Chemical Property of Methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-b-D-glucopyranoside

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:

98%Min ^*data from raw suppliers

Methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-b-D-glucopyranoside ^*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

Technology Process of Methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-b-D-glucopyranoside

There total 25 articles about Methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-b-D-glucopyranoside 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 4,6-O-Benzylidene-β-D-manno-pyranoside

methyl 3-O-benzoyl-4,6-O-benzylidene-β-D-mannopyranoside

methyl 2-O-benzoyl-4,6-O-benzylidene-β-D-mannopyranoside

methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-mannopyranoside

Refernces

• 1、 Dong, Hai,Feng, Guang-Jing,Luo, Tao,Lv, Jian,Yu, Jian-Cheng. "Stannous chloride as a low toxicity and extremely cheap catalyst for regio-/site-selective acylation with unusually broad substrate scope". supporting information. p. 6936 - 6942. Retrieved 2020/11/09.
• 2、 Tong, My Linh,Huber, Florian,Taghuo Kaptouom, Estelle S.,Cellnik, Torsten,Kirsch, Stefan F.. "Enhanced site-selectivity in acylation reactions with substrate-optimized catalysts on solid supports". supporting information. p. 3086 - 3089. Retrieved 2017/03/17.