title: Organoboron-catalyzed regio- and stereoselective formation of β-2-deoxyglycosidic linkages.
abstract: A borinic acid derived catalyst enables regioselective and β-selective reactions of 2-deoxy- and 2,6-dideoxyglycosyl chloride donors with pyranoside-derived acceptors having unprotected cis-1,2- and 1,3-diol groups. The use of catalysis to promote a β-selective pathway by enhancement of acceptor nucleophilicity constitutes a distinct approach from previous work, which has been aimed at modulating donor reactivity by variation of protective and/or leaving groups.
authors: Department of Chemistry, University of Toronto , 80 St. George Street, Toronto, ON M5S 3H6, Canada.
authors: Thomas M
authors: TM
authors: Beale
authors: Patrick J
authors: PJ
authors: Moon
authors: Mark S
authors: MS
authors: Taylor
mesh_terms: D001889:Borinic Acids / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001889:Borinic Acids; D006027:Glycosides