21056-51-9

Upstream product

• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 154859-10-6 <2'R,2''R,6'R,6''R> methyl 6-O-(tert-butyldiphenylsilyl)-2-O,3-O-(6',6''-diphenyloctahydro-2',2''-bipyran-2',2''-diyl)-α-D-glucopyranoside 
• 58479-62-2 (2R,3S,4S,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol 
• 154859-12-8 <2'R,2''R,6'R,6''R> methyl 4-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-2-O,3-O-(6',6''-diphenyloctahydro-2',2''-bipyran-2',2''-diyl)-α-D-glucopyranoside 

Relevant academic research and scientific papers

Lead-Catalyzed Aqueous Benzoylation of Carbohydrates with an Acyl Phosphate Ester

Biochemical systems utilize adenylates of amino acids to aminoacylate the 3′-terminal diols of tRNAs. The reactive acyl group of the biological acylation agent is a subset of the general class of acyl phosphate monoesters. Those compounds are relatively stable in aqueous solutions, and their alkyl esters are conveniently prepared. It has previously been shown that biomimetic reactions of acyl phosphate monoesters with diols and carbohydrates are promoted by lanthanide salts. However, they also promote hydrolysis of acyl phosphate reagents, and the overall yields are modest. An assessment of the catalytic potential of alternative Lewis acids reveals that lead ions may be more effective as catalysts than lanthanides. Treatment of carbohydrates with benzoyl methyl phosphate (BMP) and triethylamine in water with added lead nitrate produces monobenzoyl esters in up to 75% yield. This provides a water-compatible pathway for novel patterns of benzoylation of polyhydroxylic compounds.

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.

Dispiroketals in Synthesis (Part 17): Regioselective Protection of D-Glucopyranoside, D-Galactopyranoside and D-mannopyranoside Substrates

Chiral recognition of enantiomeric trans-1,2-diol relationships leading to regioselective formation of 1,8,13,16-tetraoxadispirohexadecanes (dispiroketals) of various D-glucopyranoside, D-galactopyranoside and D-mannopyranoside substrates is desc

Dispiroketals in Synthesis (Part 8): Regioselective Protection of D-Glucopyranose Substrates.

A new process for the efficient regioselective formation of 1,8,13,16-tetraoxadispirohexadecanes (dispiroketals) of various D-glucopyranosyl substrates by the chiral recognition of enantiomeric trans 1,2-diol relationships is described.This was achieved using the novel enantiomerically pure 2,2'-disubstituted 3,3',4,4'-tetrahydro-6,6'-bi-2H-pyrans 1,2 and 11.New conditions for the removal of dispiroketal protecting groups are presented.