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Sialylation using N-glycolylneuraminyl phosphite donors to synthesize Neu5Gc-containing glycans
Authors:Shinya Hanashima  Taku Tomiya  Shoji Akai
Institution:a Material and Life Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Yokohama 221-8686, Japan
b Structural Glycobiology Team, Systems Glycobiology Research Group, RIKEN Advanced Science Institutes, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan
Abstract:Efficient sialylations using N-glycolylneuraminic acid (Neu5Gc) phosphite donors having an acetyl or benzyl group on the glycolyl moiety are described in the synthesis of Neu5Gc-containing glycans. Both phosphite donors 1 and 2 were readily coupled with primary and secondary acceptor alcohols in propionitrile at −78 °C to provide the desired glycosides with good α-selectivities.
Keywords:N-Glycolylneuraminic acid  Sialic acid  Glycosylation  Phosphite
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