80245-09-6

Basic information

• Product Name: methyl 4,6-di-O-benzoyl-β-D-glucopyranoside
• Synonyms: methyl 4,6-di-O-benzoyl-β-D-glucopyranoside
• CAS NO: 80245-09-6
• Molecular Weight: 402.401
• Mol File: 80245-09-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: methyl 4,6-di-O-benzoyl-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4,6-di-O-benzoyl-β-D-glucopyranoside(80245-09-6)
• EPA Substance Registry System: methyl 4,6-di-O-benzoyl-β-D-glucopyranoside(80245-09-6)

Safety Data

• Hazardous Substances Data: 80245-09-6(Hazardous Substances Data)

Upstream product

• 6605-40-9 methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 98-88-4 benzoyl chloride 
• 71117-37-8 (2R,4aR,6R,7R,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 95821-86-6 methyl-(O²,O³-diacetyl-O⁴,O⁶-dibenzoyl-β-D-glucopyranoside) 

Relevant articles and documents

Site-selective and stereoselective O-alkylation of glycosides by Rh(II)-catalyzed carbenoid insertion

Carbohydrates are synthetically challenging molecules with vital biological roles in all living systems. Selective synthesis and functionalization of carbohydrates provide tremendous opportunities to improve our understanding on the biological functions of this fundamentally important class of molecules. However, selective functionalization of seemingly identical hydroxyl groups in carbohydrates remains a long-standing challenge in chemical synthesis. We herein describe a practical and predictable method for the site-selective and stereoselective alkylation of carbohydrate hydroxyl groups via Rh(II)-catalyzed insertion of metal carbenoid intermediates. This represents one of the mildest alkylation methods for the systematic modification of carbohydrates. Density functional theory (DFT) calculations suggest that the site selectivity is determined in the Rh(II)-carbenoid insertion step, which prefers insertion into hydroxyl groups with an adjacent axial substituent. The subsequent intramolecular enolate protonation determines the unexpected high stereoselectivity. The most prevalent trans-1,2-diols in various pyranoses can be systematically and predictably differentiated based on the model derived from DFT calculations. We also demonstrated that the selective O-alkylation method could significantly improve the efficiency and stereoselectivity of glycosylation reactions. The alkyl groups introduced to carbohydrates by OH insertion reaction can serve as functional groups, protecting groups, and directing groups.

A facile chemoselective deacetylation in the presence of benzoyl and p-bromobenzoyl groups using p-toluenesulfonic acid

The acetyl group was chemoselectively cleaved in the presence of p-toluenesulfonic acid (p-TsOH) in CH2Cl2/MeOH without affecting the benzoyl (benzoate and p-bromobenzoate) groups and no transesterification product was observed. The treatment of protected carbohydrates with p-TsOH·H2O at room temperature usually required a longer reaction time than at 40°C. Other types of sulfonic acid such as 10-camphorsulfonic (CSA) led to similar results.