Synthesis of Hexenuloses and a Library of Disaccharides Possessing 3-oxo-glycal Unit

An expeditious method for the synthesis of monosaccharides and disaccharides possessing 3-oxo-glycal units is revealed. Several monosaccharides and disaccharide-derived glycals are converted to the corresponding hexenuloses in three steps involving halo-alkoxylat ion, dehydrohalogenation, and ketalyzation reactions. A number of 3-oxo-glycals are synthesized to show the methodology's importance and generality. Further, the protocol is successfully applied to synthesize a rare-sugar disaccharide donor unit present as part of the trisaccharide moiety in the reported natural product, versipelostatin.

Automated summary

This study reveals an expeditious method for synthesizing monosaccharides and disaccharides with 3-oxo-glycal units. Several monosaccharides and disaccharide-derived glycals are converted to the corresponding hexenuloses through three steps involving halo-alkoxylate ion, dehydrohalogenation, and ketalyzation reactions. The importance and generality of the methodology are demonstrated by the synthesis of various 3-oxo-glycals. Additionally, the protocol is successfully applied to synthesize a rare-sugar disaccharide donor unit found in the reported natural product versipelostatin.