Synthesis of allopurinol and 4-amino-1H-pyrazolo[3,4-d]pyrimidine N1- and N2-(β-D-arabinofuranosides)

Autor(en): Seela, F.
Winter, H.
Stichwörter: Adenosine deaminase; D-Arabinonucleosides; Glycosylation, nucleobase-anion; Phase-transfer catalysis; Pyrazolo[3,4-d]pyrimidines
Erscheinungsdatum: 1991
Journal: Liebigs Annalen der Chemie
Volumen: 1991
Ausgabe: 2
Startseite: 105
Seitenende: 109
Allopurinol and 4-amino-1H-pyrazolo[3,4-d]pyrimidine N1-and N2-(D-arabinofuranosides) have been synthesized. Nucleobase anion glycosylation of 4-methoxy-1H-pyrazolo[3,4-d]-pyrimidine (7) with the α-D-arabinofuranosyl chloride 6a proceeds stereoselectively and affords the N1-(β-D-nucleoside) 8 as the main product (43% yield) together with the N2 isomer 10 (25% yield). The formation of the α anomer 9 (6% yield) results from the β-D-arabinofuranosyl chloride 6b being formed upon chlorination of the nitrobenzoate 5. Compounds were deprotected (11–13) and subjected to nucleophilic displacement reactions affording allopurinol and 8-aza-7-deazaadenine N1-and N2-(arabinonucleosides) 1b, 2b, 3, and 4b. The anomeric configuration and the position of glycosylation have been established by 1D 1H-NOE difference spectroscopy. Compound 3 has proved to be a substrate of adenosine deaminase with a half-life 100-fold longer than that of ara-A. Copyright © 1991 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN: 01702041
DOI: 10.1002/jlac.199119910120
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