[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.
Carbohydrates U 0500A Facile Method for β-Selenoglycoside Synthesis Using β-p-Methylbenzoyl Selenoglycoside as the Selenating Unit. -Acylseleno glycosides (I) and (VI) are activated by the action of a secondary amine and Cs2CO3 to produce an anomeric selenolate anion, which reacts in situ with various electrophiles. Novel selenoglycosides including selenooligosaccharides and selenoglycosylamine are obtained with retention of anomeric stereochemistry. -(KAWAI, Y.; ANDO, H.; OZEKI, H.; KOKETSU, M.; ISHIHARA*, H.; Org. Lett. 7 (2005) 21, 4653-4656; Dep. Chem., Fac. Eng., Gifu Univ., Yanagido, Gifu 501-11, Japan; Eng.) -Klein 09-202
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