7-Halogenated 7-Deaza-2′-deoxyinosines

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‐toluo...

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Bibliographic Details
Published inHelvetica chimica acta Vol. 82; no. 1; pp. 12 - 18
Main Authors Ramzaeva, Natalya, Mittelbach, Cathrin, Seela, Frank
Format Journal Article
LanguageEnglish
Published Basel Verlag Helvetica Chimica Acta 13.01.1999
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
DNA
NUCLEOSIDES
OLIGONUCLEOTIDES
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Summary: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.
Bibliography:ArticleID:HLCA12
istex:5954C3AAA50B5F3078682B09C8D8C35C1307E5CE
ark:/67375/WNG-HGFSLHWP-K
ISSN:0018-019X
1522-2675
DOI:10.1002/(SICI)1522-2675(19990113)82:1<12::AID-HLCA12>3.0.CO;2-L