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7‐Halogenated 7‐Deaza‐2′‐deoxyinosines
Author(s) -
Ramzaeva Natalya,
Mittelbach Cathrin,
Seela Frank
Publication year - 1999
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/(sici)1522-2675(19990113)82:1<12::aid-hlca12>3.0.co;2-l
Subject(s) - chemistry , glycosylation , diastereomer , stereochemistry , chloride , medicinal chemistry , organic chemistry , biochemistry
Abstract The synthesis of the 7‐deaza‐2′‐deoxyinosine derivatives 3a – c with chloro, bromo, and iodo substituents at position 7 is described. Glycosylation of the 7‐halogenated 6‐chloro‐7‐deazapurines 4a – c or of the 7‐halogenated 6‐chloro‐7‐deaza‐2‐(methylthio)purines 9a – c with 2‐deoxy‐3,5‐di‐ O ‐(4‐toluoyl)‐ α ‐ D ‐ erythro ‐pentofuranosyl chloride ( 5 ) furnished the intermediates 7a – c and 11a – c , respectively, which gave, upon deprotection, the desired nucleosides 3a – c .