Synthesis of 2′‐Deoxyisoinosine and Related 2′‐Deoxyribonucleosides | Zendy

Seela Frank | Zendy; Chen Yaoming | Zendy; Bindig Uwe | Zendy; Kazimierczuk Zygmunt | Zendy

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Synthesis of 2′‐Deoxyisoinosine and Related 2′‐Deoxyribonucleosides

Author(s) -

Seela Frank,

Chen Yaoming,

Bindig Uwe,

Kazimierczuk Zygmunt

Publication year - 1994

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.19940770122

Subject(s) - deoxyribonucleosides , chemistry , pyrimidine , nucleobase , deoxyguanosine , purine , glycosylation , stereochemistry , derivative (finance) , stereoselectivity , fluorescence , deoxyribonucleoside , dna , combinatorial chemistry , organic chemistry , biochemistry , catalysis , financial economics , economics , enzyme , physics , quantum mechanics

Various 2‐substituted purine and pyrrolo[2,3‐ d ]pyrimidine 2′‐deoxyribonucleosides with methylthio ( 13a ), chloro ( 13b ), methoxy ( 9b ), and oxo ( 2, 3 ) substituents at C(2) are prepared. They are obtained either via stereoselective nucleobase‐anion glycosylation or by base transformation. A three‐step synthesis of the unknown 2′‐deoxyisoinosine ( 2 ) from 2′‐deoxyguanosine ( 15 ) is described. Compound 2 as well as its 7‐deazapurine derivative 3 exhibit strong fluorescence.

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