Glycosylation of l,4:3,6-dianhydro-D-glucitol (isosorbide).
Condensation of 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl-, 2,3,4-tri-O-acetyl-alpha-D-xylopyranosyl- and of 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromides with l,4:3,6-dianhydro-D-glucitol under Koenigs-Knorr conditions, and using the Helferich modification of the reaction showed regioselectivity in glysosylation at C-5 of isosorbide.
Claffey
David J
DJ
Chemistry Department, National University of Ireland, Galway, Ireland.
Casey
Mary F
MF
Finan
Patrick A
PA
D001965:Bromides / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D007547:Isosorbide / Q000737:chemistry*; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry
D001965:Bromides; D006027:Glycosides; D009005:Monosaccharides; D007547:Isosorbide