81712-55-2

Upstream product

• 908093-98-1 diazodiphenylmethane 
• 5605-82-3 3,4,6-tri-O-acetyl-α-D-glucopyranosyl chloride 
• 4451-37-0 3,4,6-tri-O-acetyl-β-D-glucopyranosyl chloride 
• 81712-54-1 3,4,6-tri-O-acetyl-2-O-diphenylmethyl-α-D-glucopyranosyl chloride 
• 4692-12-0 1,3,4,6-tetra-O-acetyl glucopyranose 

Relevant academic research and scientific papers

DIPHENYLMETHYLATION OF CARBOHYDRATE HYDROXYL GROUPS BY THE REACTION WITH DIAZO(DIPHENYL)METHANE

Diphenylmetylation of carbohydrate hydroxyl groups may be effected by the thermal reaction with diazo(diphenyl)methane in absence of catalysts.Migration of the labile ester groups of methyl 2,3,4-tri-O-acetyl-α-D-glucopyranoside and 3-O-benzoyl-1,2-O-isopropylidene-α-D-glucofuranose does not occur during diphenylmethylation by this procedure.The diphenylmethyl group may be readily removed by catalytic hydrogenolysis, and is sufficiently acid-stable to enable the selective hydrolysis of acetal groups.Its use as an O-4 protecting-group and as a non-participating O-2 protecting-group in α-glucoside synthesis has been demonstrated in syntheses of methyl 2,3,6-tri-O-methyl-α-D-glucopyranoside and kojibiose octa-acetate, respectively.