Stereoselective synthesis of 2-S-phenyl-2-deoxy-beta-glycosides using phenyl 2,3-O-thionocarbonyl-1-thioglycoside donors via 1,2-Migration and concurrent glycosidation.
[figure: see text] 1,2-Migration and concurrent glycosidation of phenyl 2,3-O-thionocarbonyl-1-thlo-alpha-L-rhamnopyranosides under the action of methyl trifluoromethanesulfonate (MeOTf) afforded in high yields the 3-O-(methylthio)carbonyl-2-S-phenyl-2,6-dideoxy-beta-L-glucopyranosides, ready precursors to the corresponding 2-deoxy-beta-glycosides.
Yu
B
B
State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China. byu@pub.sioc.ac.cn
Yang
Z
Z
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D002240:Carbohydrate Sequence; D002301:Cardiac Glycosides / Q000138:chemical synthesis; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D008969:Molecular Sequence Data; D013237:Stereoisomerism; D013865:Thioglycosides / Q000737:chemistry*
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D002301:Cardiac Glycosides; D006027:Glycosides; D013865:Thioglycosides