Facile Preparation of a Phenyl 1-Thioglycoside of Allopyranosylallopyranose from Allyl N,N′-Diacetylchitobioside

An allopyranosyl analog of allyl N,N′-diacetylchitobioside was converted to the corresponding N,N′-diphthaloylated glycosyl acetate in good yield. A thioglycosidation reaction of the glycosyl acetate gave phenyl 3,6-di-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-allopyranoside, the key intermediate employed in the total synthesis of an insect chitinase inhibitor, allosamidin.

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