Synthesis of Acyclic C-Nucleoside Analogues Using (E)-1,2-Dideoxy-1-dimethylamino-4,5:6,7-di-O-isopropylidene-d-arabino-hept-1-en-3-ulose

1-Deoxy-3,4:5,6-di-O-isopropylidene-d-arabino-hex-2-ulose reacted with N,N-dimethylformamide dimethyl acetal and tert-butoxy[bis(dimethylamino)]methane, respectively, to furnish (E)-1,2-dideoxy-1-dimethylamino-4,5:6,7-di-O-isopropylidene-d-arabino-hept-1-en-3-ulose. This push-pull activated heptenul...

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Bibliographic Details
Published in:Journal of carbohydrate chemistry 2003-12, Vol.22 (7-8), p.537-548
Main Authors: Methling, Karen, Kopf, Jürgen, Michalik, Manfred, Reinke, Helmut, Bürger, Christiane, Oberender, Heiderose, Peseke, Klaus
Format: Article
Language:English
Subjects:
C-Nucleoside analogues
Heptenuloses
Push-pull alkenes
Pyrazoles
Pyrimidines
Tetritols
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Summary:1-Deoxy-3,4:5,6-di-O-isopropylidene-d-arabino-hex-2-ulose reacted with N,N-dimethylformamide dimethyl acetal and tert-butoxy[bis(dimethylamino)]methane, respectively, to furnish (E)-1,2-dideoxy-1-dimethylamino-4,5:6,7-di-O-isopropylidene-d-arabino-hept-1-en-3-ulose. This push-pull activated heptenulose underwent ring closure reactions with various N,N′-nucleophiles like hydrazine hydrate, amidinium, guanidinium and isothiouronium salts in the presence of bases to yield pyrazole and pyrimidine derivatives, respectively, all of which derivatized with a di-O-isopropylidenated tetritol side chain. The isopropylidene groups were removed with methanolic HCl in the pyrazole series, whereas aq TFA was used in the case of pyrimidine analogues. † This paper is dedicated to Professor Dr. Gérard Descotes on the occasion of his 70th birthday
ISSN:0732-8303
1532-2327
DOI:10.1081/CAR-120026457