Stereospecific synthesis of beta-D-allopyranosides by dihydroxylation of beta-D-erythro-2,3-dideoxyhex-2-enopyranosides.
The synthesis of 4,6-O-benzylidene-beta-D-erythro-2-3-dideoxyhex-2-enopyranosides and their osmium and ruthenium catalysed dihydroxylation reactions have been investigated. These reactions have been shown, for a range of monosaccharides and a disaccharide, to proceed stereospecifically to give beta-D-allopyranosides in moderate to excellent yield.
Murphy
P V
PV
Department of Chemistry, Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Belfield, 4, Dublin, Ireland. paul.v.murphy@ucd.ie
O'Brien
J L
JL
Smith
A B
AB
D002384:Catalysis; D004187:Disaccharides / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis*; D006900:Hydroxylation; D009992:Osmium / Q000737:chemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis*; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
C438448:4,6-O-benzylidene-erythro-2-3-dideoxyhex-2-enopyranoside; D004187:Disaccharides; D006027:Glycosides; D011083:Polycyclic Compounds; D009992:Osmium; D012428:Ruthenium