title: A facile method for beta-selenoglycoside synthesis using beta-p-methylbenzoyl selenoglycoside as the selenating unit.
abstract: [reaction: see text] The reaction between alpha-glycosyl bromides and potassium p-methylselenobenzoate yields beta-p-methylbenzoyl selenoglycosides. The acyl selenoglycosides were activated by the action of a secondary amine and Cs2CO3 to produce an anomeric selenolate anion, which reacted in situ with various electrophiles to yield novel selenoglycosides while retaining the anomeric stereochemistry.
authors.affiliation: Department of Chemistry, Faculty of Engineering, 1-1 Yanagido, Gifu 501-1193, Japan.
authors.forename: Yumiko
authors.initials: Y
authors.lastname: Kawai
authors.forename: Hiromune
authors.initials: H
authors.lastname: Ando
authors.forename: Hideya
authors.initials: H
authors.lastname: Ozeki
authors.forename: Mamoru
authors.initials: M
authors.lastname: Koketsu
authors.forename: Hideharu
authors.initials: H
authors.lastname: Ishihara
mesh_terms: D000588:Amines / Q000737:chemistry; D002384:Catalysis; D002586:Cesium / Q000737:chemistry; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000588:Amines; D005960:Glucosides; D016566:Organoselenium Compounds; D002586:Cesium