Development of Novel Glycosyl Donors for 1,2-<i>cis</i> Glycosylation Reaction for Amino Sugar and Synthesis of anti-<i>Helicobacter pylori</i> Oligosaccharide

Abstract

Despite advances in synthetic carbohydrate chemistry, the 1,2-cis-selective glycosylation reaction of 2-deoxy-2-amino sugars has not progressed during the last three decades. For such glycosylations, 2-azide glycosyl donors have been extensively employed, notwithstanding di‹cul-ties in their preparation and moderate selectivities. Herein, we report on a highly 1,2-cis-selective trans-carbamate sugar donor, which can be readily prepared in high yields. Furthermore, the utility of the novel cis-selective glycosyl donor for preparing complex oligosaccharides is demonstrated through the eŠective synthesis of an antiHelicobacter pylori hexasaccharide.

Recent Approaches to the Chemical Synthesis of Sugar Nucleoside Diphosphates

“…Chemical synthesis of naturally occurring complex oligosaccharides is increasingly more accessible due to recent progress in the development of protection (1) and glycosylation methods (2)(3)(4)(5)(6). Despite these advances, such synthesis is still time-consuming since it requires multiple steps, including protection-deprotection manipulations and region-/stereo-selective glycosylations.…”