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A facile regio- and stereo-selective synthesis of α-glycosides of N-acetylneuraminic acid

✍ Scribed by Takatoshi Murase; Hideharu Ishida; Makoto Kiso; Akira Hasegawa

Publisher
Elsevier Science
Year
1988
Tongue
English
Weight
249 KB
Volume
184
Category
Article
ISSN
0008-6215

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✦ Synopsis

Sialic acids',* are well known as constituents of glycoproteins and glycolipids of cell membranes, and they play a role in biological recognition.

It is also known that naturally occurring sialo compounds contain sialic acids in a-glycosidic linkage, except for CMP-N-acetylneuraminic acid. Therefore, a facile regio-and a-selective glycoside synthesis of N-acetylneuraminic acid (NeuSAc) is critically important, in order to investigate the structure-function relationships of such sialoglycoconjugates as glycoproteins and glycolipids. Glycosidation of methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-Dglycero-p-D-g&c&-2-nonulopyranosyl chloride)onate3 as the glycosyl donor with sugar derivatives usually gives a mixture of (Y-and P-glycosides.

When reacting with secondary hydroxyl groups of sugar derivatives, this donor affords the expected cr-glycosides in very low yields.

Recently, new effort+ have been made at obtaining mainly a-glycosides,

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