56543-18-1

Upstream product

• 2774-22-3 methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyraniside 

Relevant academic research and scientific papers

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

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.

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.

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