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An easy synthesis of methyl 4-(2,3:5,6-di-O-isopropylidene-α- and -β-d-mannofuranosyl)-3-oxobutanoate: A new approach to pyrazofurins

✍ Scribed by F.J. Lopez Herrera; C. Uraga Baelo

Publisher: Elsevier Science
Year: 1985
Tongue: English
Weight: 607 KB
Volume: 139
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(85)90010-2

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✦ Synopsis

The reaction of 2,3:5,6-di-0-isopropylidene-cu-D-mannofuranose with (3methoxycarbonyl-2-oxopropylidene)triphenylphosphorane, catalysed by benzoic acid in dry benzene, gives methyl 4-(2,3:5,6-di-O-isopropylidene-cr-and -@-mannofuranosyl)-3-oxobutanoate in good yield. These compounds are easily transformed into 4-hydroxy-3-(a-and P-D-mannofuranosyl)pyrazole-5-carboxamide, which are the mannofuranosyl analogues of pyrazofurins. The anomeric configurations of the products were assigned on the basis of *H-n.m.r. data.

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