R. T. Lee, Yuan-chuan Lee
Dec 1, 1978
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0
Influential Citations
4
Citations
Journal
Carbohydrate Research
Abstract
Abstract Methyl and benzyl 3- O -β- d -xylopyranosyl-α- d -mannopyranoside were prepared by way of d -xylosylation (Koenigs-Knorr) of methyl and benzyl 4,6- O -benzylidene-α- d -mannopyranoside ( 1 and 17 ). Analogous 2- O -β- d -xylopyranosyl-α- d -mannopyranosides could not be prepared efficiently by this procedure. However, methyl and benzyl 3- O -acetyl-4,6- O -benzylidene-α- d -mannopyranoside, prepared by limited acetylation of 1 and 17 , respectively, could be d -xylosylated by the same method, and afforded, after removal of protective groups, methyl and benzyl 2- O -β- d -xylopyranosyl-α- d -mannopyranoside. Hydrogenolysis of benzyl 2- O - and 3- O -β- d -xylopyranosyl-α- d -mannopyranoside yielded the corresponding, reducing disaccharides. In addition to these disaccharides, disaccharides containing an α- d -xylopyranosyl group, and trisaccharides having d -xylopyranosyl groups at both O-2 and O-3 were obtained as minor products.