A facile, large-scale preparation of the methyl 2-thioglycoside of N-acetylneuraminic acid, and its usefulness for the α-stereoselective synthesis of sialoglycosides

A Hasegawa, H Ohki, T Nagahama, H Ishida…

Index: Hasegawa, Akira; Ohki, Hitoshi; Nagahama, Takao; Ishida, Hideharu; Kiso, Makoto Carbohydrate Research, 1991 , vol. 212, p. 277 - 281

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Citation Number: 142

Abstract

Recently, new efforts 69 have been made towards the synthesis of a-glycosides of N- acetylneuraminic acid (NeuSAc), but the procedure still remains to be improved with respect to yields, regio-and stereo-selectivity, and potential for scale-up. We have developed'@'3 a procedure for regio-and a-stereo-selective glycosylation with sialosyl groups involving the reaction of the methyl a-thioglycosides of sialic acids as the glycosyl donors, suitably ...