✦ LIBER ✦

Facile Synthesis of 2′-Deoxyribofuranosides of Allopurinol and 4-Amino-1H-pyrazolo[3,4-d]pyrimidine via Phase-Transfer Glycosylation

✍ Scribed by Frank Seela; Herbert Steker

Publisher: John Wiley and Sons
Year: 1985
Tongue: German
Weight: 468 KB
Volume: 68
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19850680305

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✦ Synopsis

Abstract

Phase‐transfer glycosylation of 4‐methoxy‐1__H__‐pyrazolo[3,4‐d]pyrimidine with the 2‐deoxyribofuranosyl chloride 9 formed the N(1)‐β‐nucleoside 10a as main product (39%). As by‐products the α‐D‐anomer 11a (7%) and the N(2)‐isomer 12a (18%) were isolated. Assignment of these isomers was made on the basis of their ^1^H‐ and ^13^C‐NMR spectra. Removal of the sugar‐protecting groups yielded the 4‐methoxy‐nucleosides 10b, 11b, and 12b, respectively. Nucleophilic displacement of the 4‐MeO‐group gave the 2‐deoxyribofuranosides 1–4 of allopurinol and 4‐amino‐1__H__‐pyrazolo[3,4‐d]pyrimidine.

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