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Reinvestigation of the synthesis of 4-methylcoumarin-7-yl 5-acetamido-3,5-dideoxy-α-d-glycero-d-galacto-2-nonulopyranosidonic acid, a fluorogenic substrate for neuraminidase

✍ Scribed by Neil Baggett; Brian J. Marsden

Publisher
Elsevier Science
Year
1982
Tongue
English
Weight
563 KB
Volume
110
Category
Article
ISSN
0008-6215

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✦ Synopsis

A crystalline tetrabutylammonium salt of 7-hydroxy-4-methylcoumarin was prepared and shown to contain two coumarin residues for each ammonium group. Condensation of this salt with the glycosyl chloride of methyl 5-acetamido-4,7,8,9tetra-~-acetyl-3,5-ddeoxy-~-D~~ycero-D-gu~acto-2-non~opyr~osona~ in dry iK&Onitrile at room temperature gave the corresponding a-glycoside in higher yield and purity than previously reported methods. Removal of the acetyl and methyl ester blocking-groups gave the free glycoside, which was shown to have the CI configuration by n.m.r. spectroscopy. In contrast, the reaction of the free coumarin derivative with the chloro sugar in refluxing, dry toluene in the presence of cadmium carbonate as acid acceptor gave none of the above glycoside, but gave the corresponding glycal in good yield.

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