Stereoselective synthesis of various α-selenoglycosides using in situ production of α-selenolate anion

A large variety of alpha-selenoglycosides, including alkyl and aryl selenoglycosides, selenoglycosyl amino acid and selenodisaccharide have been synthesized in a stereoselective manner. The key precursor of alpha-anomeric selenolate anion was designed as p-methylbenzoyl selenoglycoside, which was synthesized by the reaction of beta-glycosyl chloride with potassium p-methylselenobenzoate. Upon the action of piperazine or methylhydrazine in the presence Of Cs2CO3, the acyl selenoglycoside produced an anomeric selenolate anion, which reacted in situ with various electrophilic counterparts to yield alpha-selenoglycoside. (c) 2006 Elsevier Ltd. All rights reserved.