SYNTHETIC STUDIES ON SIALOGLYCOCONJUGATES-53 - SYNTHESIS OF NOVEL N-METHYL-1-DEOXYNOJIRIMYCIN-CONTAINING SIALO-OLIGOSACCHARIDES RELATED TO GANGLIOSIDE GM3 ACTIVE AS A BIOSIGNAL MEDIATOR
M. Kiso et al., SYNTHETIC STUDIES ON SIALOGLYCOCONJUGATES-53 - SYNTHESIS OF NOVEL N-METHYL-1-DEOXYNOJIRIMYCIN-CONTAINING SIALO-OLIGOSACCHARIDES RELATED TO GANGLIOSIDE GM3 ACTIVE AS A BIOSIGNAL MEDIATOR, Journal of carbohydrate chemistry, 13(2), 1994, pp. 163-174
O-(6-O-Benzoyl-beta-D-galactopyranosyl)-(1-->4)- and O-(2,3,4-tri-O-ac
etyl-beta-D-galactopyranosyl)- enzyloxycarbonyl-1,5-dideoxy-1,5-imino-
D-glucitols (4 and 12) were each coupled with methyl (methyl 5-acetami
do-4,7,8, 9-tetra-O-acetyl-3, 2-thio-D-glycero-D-galacto-2-nonulopyran
osid)onate (5) in acetonitrile medium in the presence of dimethyl(meth
ylthio)sulfonium triflate (DMTST) or N-iodosuccinimide/trifluoromethan
esulfonic acid to give the corresponding alpha-sialyl-(2-->3)- and alp
ha-sialyl-(2-->6)-glycosides (6 and 13 alpha), which were converted to
novel ganglioside GM3-related trisaccharides (9 and 15) containing N-
methyl-1-deoxynojirimycin.