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

Seela Frank | Zendy; Steker Herbert | Zendy

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

Author(s) -

Seela Frank,

Steker Herbert

Publication year - 1985

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19850680305

Subject(s) - chemistry , pyrimidine , glycosylation , nucleophile , stereochemistry , nucleoside , deoxyribonucleoside , anomer , nucleic acid , protecting group , organic chemistry , catalysis , dna , biochemistry , alkyl

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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