Premium
Synthesis of 8‐Aza‐1,3‐dideaza‐2′‐deoxyadenosine and 5,6‐Disubstituted Benzotriazole 2′‐Deoxy‐β‐ D ‐Ribofuranosides via Nucleobase‐Anion Glycosylation
Author(s) -
Kazimierczuk Zygmunt,
Seela Frank
Publication year - 1990
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.19900730211
Subject(s) - chemistry , benzotriazole , nucleobase , anomer , glycosylation , stereochemistry , deoxyadenosine , glycosyl , stereoselectivity , nucleoside , organic chemistry , dna , catalysis , biochemistry , enzyme
Abstract The synthesis of 8‐aza‐1,3‐dideaza‐2′‐deoxyadenosine ( 3a ) as well as of 4‐ and 5,6‐substituted benzotriazole 2′‐deoxy‐β‐ D ‐ribonucleosides is described ( Schemes 1–3 ). Glycosylation of benzotriazole anions is stereoselective in all cases (exclusive β‐ D ‐anomer formation), but regioisomeric N 1 , N 2 , and N 3 ‐(2′‐deoxyribofuranosides) are formed. The distribution of the regioisomers is controlled by the nucleobase substituents. Anomeric configuration as well as the position of glycosylation are determined by UV and NMR in combination with 1D‐NOE‐difference spectroscopy. The unprotonated forms of 4‐aminobenzotriazoic 2′‐deoxy‐β‐ D ‐ribofuranosides 3a – c exhibit strong fluorescence.