A facile method for beta-selenoglycoside synthesis using beta-p-methylbenzoyl selenoglycoside as the selenating unit.
[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.
Kawai
Yumiko
Y
Department of Chemistry, Faculty of Engineering, 1-1 Yanagido, Gifu 501-1193, Japan.
Ando
Hiromune
H
Ozeki
Hideya
H
Koketsu
Mamoru
M
Ishihara
Hideharu
H
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
D000588:Amines; D005960:Glucosides; D016566:Organoselenium Compounds; D002586:Cesium