29868-43-7

Basic information

• Product Name: methyl 2,3-di-O-acetyl-6-O-benzoyl-α-D-glucopyranoside
• Synonyms: methyl 2,3-di-O-acetyl-6-O-benzoyl-α-D-glucopyranoside
• CAS NO: 29868-43-7
• Molecular Weight: 382.367
• Mol File: 29868-43-7.mol

Chemical Properties

• CAS DataBase Reference: methyl 2,3-di-O-acetyl-6-O-benzoyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3-di-O-acetyl-6-O-benzoyl-α-D-glucopyranoside(29868-43-7)
• EPA Substance Registry System: methyl 2,3-di-O-acetyl-6-O-benzoyl-α-D-glucopyranoside(29868-43-7)

Safety Data

• Hazardous Substances Data: 29868-43-7(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 29868-42-6 methyl 2,3-di-O-acetyl-α-D-glucopyranoside 
• 2774-22-3 methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyraniside 

Relevant articles and documents

Facile cleavage of carbohydrate benzyl ethers and benzylidene acetals using the NaBrO3/Na2S2O4 reagent under two-phase conditions

Benzyl ether and benzylidene acetal carbohydrate protecting groups can be selectively cleaved by reaction with sodium bromate/sodium dithionite in ethyl acetate/water. Under the mild (room temperature, short reaction time) conditions needed, a variety of other protecting functionalities such as acetyl, chloroacetyl, benzoyl, pivaloyl, tosyl, t-butyldimethylsilyl, trityl, and isopropylidene groups remain unaffected.

Facile oxidative cleavage of benzylidene acetals using molecular oxygen catalyzed by N-hydroxyphthalimide/Co(OAc)2

Benzylidene acetals derived from 1,2- and 1,3-diols undergo facile oxidative cleavage to give hydroxy benzoate esters with molecular oxygen in the presence of catalytic amount of N-hydroxyphthalimide/Co(OAc)2.

Regioselective oxidative cleavage of benzylidene acetals of glycopyranosides with periodic acid catalyzed by tetrabutylammonium bromide

A combination of periodic acid, tetrabutylammonium bromide, and wet alumina in dichloromethane efficiently oxidized benzylidene acetals of carbohydrates to the corresponding hydroxybenzoates in excellent yields (>90%). Under these conditions, other protec

Glycosylated eumelanin building blocks by thioglycosylation of 5,6-diacetoxyindole with an expedient selenium-based dynamic-mixture methodology

A series of 3-thioglycosylated 5,6-diacetoxyindole derivatives, which are important tools for eumelanin research and application, were prepared through a practical and efficient approach exploiting a dynamic mixture of thioglycoside agents. The strategy is feasible for installing both mono- and disaccharide units and relies on the facile in situ conversion of glycosyl disulfides into the corresponding, more reactive, phenylselenenyl sulfides in the presence of diphenyl diselenide, N-bromosuccinimide (NBS) and tetrabutylammonium bromide (TBAB). An expedient thioglycosidation of 5,6-diacetoxyindole with a dynamic mixture of thioglycosides is described. Copyright

Regioselective control in the oxidative cleavage of 4,6-o-benzylidene acetals of glycopyranosides by dimethyldioxirane

"Chemical Equation Presentation" The oxidative cleavage of 4,6-O-benzylidene acetals of glycopyranosides using dimethyldioxirane (DMDO) leads to the corresponding hydroxy-benzoates in excellent yields. With a proper choice of the neighboring protecting groups, this oxidative fragmentation provides the 6- or 4-hydroxyl derivatives in a highly regioselective manner.

Regioselective oxidative cleavage of benzylidene acetals: synthesis of highly functionalized chiral intermediates

A mild and efficient method for the regioselective oxidative cleavage of benzylidene acetals with KBrO3/Na2S2O4 under bi-phasic conditions (EtOAc/H2O), leading to highly functionalized chiral intermed

Acylation of carbohydrates over Al2O3: Preparation of partially and fully acylated carbohydrate derivatives and acetylated glycosyl chlorides

Selective and per-O-acylation of carbohydrate derivatives using acyl chlorides and Al2O3, a solid support reagent, is reported. This protocol does not require the addition of any base or activator. This methodology has been further extended to the selective acylation of carbohydrate diols and the one-pot preparation of acetylated glycosyl chlorides direct from free reducing sugars. The yields obtained in most of the cases are excellent.

Oxidative Cleavage of 4,6-O-Benzylidene Ring with t-Butyl Hydroperoxide and Copper(II) Chloride. Preparation of Methyl 4-O- and 6-O-Benzoylhexopyranoside Derivatives

Copper(II) chloride and palladium(II) acetate were found to be highly effective catalysts for oxidative cleavage of O-benzylidene ring with t-butyl hydroperoxide.Using the former catalyst 4,6-O-benzylidenehexopyranoside derivatives were converted into the