A Novel Approach to #beta#-(1->4)-Linked Thiodisaccharides Starting from Disulfide Sugars

摘要

Glycosylation of monosaccharides 4,8, and 10 containing an intramolecular disulfide bridge by applying Helferich-conditions and an excess of acetobromohexose 5 or 11 as donor substrate yielded 6-thiocyanato-#beta#-(1- > 4)-thiodisaccharides 6,9, and 12 regio- and stereospecifically in moderate to good yields. In addition, the formation of trisaccharides 7 and 13 could be observed, albeit in low yield. This novel route for thioglycoside formation may open access to a variety of bioactive disaccharide analogues.