Use of phenyl 2-alpha-selenoglycosides of N-acetylneuraminic acid as a glycosyl donor for the glycosylation reactions.
Phenyl 2-alpha-selenoglycosides of Neu5Ac were successfully prepared from the corresponding peracetylated chloro derivative of Neu5Ac 1 and phenylselenol in the presence of N,N-di-isopropylethylamine in excellent yields. The reaction of with various alcohols was effectively catalyzed by NIS/TfOH or DMTST to produce a variety of glycosides in moderate yields. Selective activation of over phenyl 2-alpha-thioglycoside of Neu5Ac with AgOTf/K(2)CO(3) was also achieved.
Ikeda
Kiyoshi
K
School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka, Japan. ikeda@ys2.u-shizuoka-ken.ac.jp
Sugiyama
Yuji
Y
Tanaka
Kiyoshi
K
Sato
Masayuki
M
D006027:Glycosides / Q000138:chemical synthesis; D006031:Glycosylation; D019158:N-Acetylneuraminic Acid / Q000031:analogs & derivatives*; D018036:Selenium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D006027:Glycosides; D018036:Selenium Compounds; D019158:N-Acetylneuraminic Acid