Synthesis of aryl-2-deoxy-D-lyxo/arabino-hexopyranosides from 2-deoxy-1-thioglycosides.
The synthesis of either anomers of aryl 2-deoxy-D-glycopyranosides from 2-deoxy-1-thioglycosides is reported. The alpha-anomers form as the major product when thioglycosides react with differently substituted phenols and naphthols, in the presence of N-iodosuccinimide/triflic acid. On the other hand, reaction of the thioglycosides with bromine initially, followed by reaction with aryloxy anions lead to aryl 2-deoxy-beta-D-glycosides with high specificities.
Paul
Somak
S
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India.
Jayaraman
Narayanaswamy
N
D001089:Arabinose / Q000737:chemistry*; D002240:Carbohydrate Sequence; D018360:Crystallography, X-Ray; D003837:Deoxy Sugars / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry; D010636:Phenols / Q000737:chemistry; D013865:Thioglycosides / Q000737:chemistry*
D003837:Deoxy Sugars; D006027:Glycosides; D009284:Naphthols; D010636:Phenols; D013865:Thioglycosides; D001089:Arabinose