S. A. Holick, S. H. Chiu, L. Anderson
Sep 1, 1976
Citations
0
Influential Citations
28
Citations
Journal
Carbohydrate Research
Abstract
Abstract 2,3,4-Tri- O -benzyl ( 11 ) and 2,3,6-tri- O -benzyl ( 12 ) -1-thio- D -glucopyranose were prepared as intermediates for the synthesis, by the thioglycoside scheme, of(1→6)- and (1→4)-linked oligosaccharides of D -glucose. The 6-hydroxyl isomer 11 was S -benzylated to the thioglucoside 13 , which is a model for a partially benzyl-protected sugar attached to a macromolecular support by a benzyl thioglycoside linkage. This linkage in 13 is readily cleaved by methyl iodide plus a nucleophile in acetone or benzene. The “alcoholysis” coupling of 13 with 6- O -acetyl-2,3,4-tri- O -benzyl-α- D -glucopyranosyl bromide gave largely the α-linked product (isomaltoside), together with a little β-linked isomer (gentiobioside).