Stereoselective synthesis of various α-selenoglycosides using in situ production of α-selenolate anion |
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| Authors: | Masahiro Nanami Yumiko Kawai Hideharu Ishihara |
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| Institution: | a Department of Chemistry, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
b Division of Instrumental Analysis, Life Science Research Center, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan |
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| Abstract: | A large variety of α-selenoglycosides, including alkyl and aryl selenoglycosides, selenoglycosyl amino acid and selenodisaccharide have been synthesized in a stereoselective manner. The key precursor of α-anomeric selenolate anion was designed as p-methylbenzoyl selenoglycoside, which was synthesized by the reaction of β-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 α-selenoglycoside. |
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| Keywords: | α-Selenoglycoside Pseudoglycoside Stereoselective synthesis |
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