Carbohydrate research

Syntheses of model oligosaccharides of biological significance. Synthesis of methyl 3, 6-di-O-(α-D-mannopyranosyl)-α-d-mannopyranoside and the corresponding …

FM Winnik, JR Brisson, JP Carver, JJ Krepinsky

Index: Winnik; Brisson; Carver; Krepinsky Carbohydrate research, 1982 , vol. 103, # 1 p. 15 - 28

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Citation Number: 40

Abstract

Abstract Methyl 2-O-allyl-4, 6-O-benzylidene-3-O-(2, 3, 4, 6-tetra-O-acetyl-α-d- mannopyranosyl)-α-d-mannopyranoside (12) was prepared in 90% yield by Helferich glycosylation of methyl 2-O-allyl-4, 6-O-benzylidene-α-d-mannopyranoside (9) with tetra-O- acetyl-α-d-mannopyranosyl bromide (11). Removal of the benzylidene group and second Helferich glycosylation with 11 led to methyl 2-O-allyl-3, 6-di-O-(2, 3, 4, 6-tetra-O-acetyl-α- ...