201534-23-8

Upstream product

• 93382-48-0 allyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 98-88-4 benzoyl chloride 
• 65987-12-4 1-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside 

Downstream Products

• 482582-74-1 C₃₀H₃₀O₈ 
• 313220-25-6 allyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside 
• 263550-38-5 allyl 3-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 155786-53-1 allyl 2,3-di-O-benzoyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

Regioselective benzoylation of 6-O-protected and 4,6-O-diprotected hexopyranosides as promoted by chiral and achiral ditertiary 1,2-diamines

Monobenzoylation of triols (6-O-silylated glycopyranosides) or diols (4,6-O-benzylidenated glycopyranosides) with benzoyl chloride and triethylamine at - 60° to 23° is promoted by catalytic amounts of ditertiary 1,2-diamines. The regioselectivity depends

Solid-phase synthesis of oligosaccharides using novel alkyne-type linkers: Selection of reactive sites on the support by Sonogashira reaction

Two new alkyne-type linkers having alkynylmethyloxy moieties were elaborated for solid-phase synthesis of oligosaccharides. A propargyl glycoside-type linker between a sugar residue and a solid support was formed by the Sonogashira reaction of a propargyl glycoside with polymer-supported iodobenzene. A propargyl ester-type linker was also constructed by the same reaction of a 4-(proparygyloxycarbonyl)benzyl glycoside with the latter. Both linkers are stable against acids such as TFA but can be readily cleaved with this acid after conversion to the corresponding alkyne-cobalt complex by treatment with C02(CO)8. The latter ester linker is generally advantageous in that mild cleavage liberates a product as its carboxybenzyl glycoside which is readily purified. The Sonogashira reaction was found to proceed only at spatially reactive sites on the solid support where the reagent accesses readily, so that the subsequent reactions including glycosylation on solid phase proceeded smoothly to result in high total yields of the desired oligosaccharides.

A facile synthesis of the tetrasaccharide repeating unit of mannoglucan from Microellobosporia grisea

A facile synthesis of the tetrasaccharide repeating unit of mannoglucan from Microellobosporia grisea was achieved through coupling of 4,6-O-benzylidene-1,2-O-ethylidene-α-D-glucopyranose with per-O-benzoylated mannopyranosyl trichloroacetimidate, followed by debenzylidenation, selective 6-O-mannopyranosylation, then hydrolysis of the 1,2-O-ethylidene group, 1,2-O-acetylation and conversion to the 1-trichloroacetimidate, and subsequent condensation of the activated trisaccharide with allyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside. (C) 2000 Elsevier Science Ltd.