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Stereoselective synthesis of 2‐azapurine 2′‐deoxy‐β‐ D ‐ribonucleosides by nucleobase‐anion glycosylation
Author(s) -
Kazimierczuk Zygmunt,
Seela Frank
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1990199001123
Subject(s) - chemistry , nucleobase , anomer , glycosylation , stereochemistry , stereoselectivity , adenosine deaminase , substrate (aquarium) , structural isomer , purine , diastereomer , nuclear magnetic resonance spectroscopy , adenosine , dna , enzyme , organic chemistry , biochemistry , catalysis , oceanography , geology
Nucleobase‐anion glycosylation of 6‐(methylthio)‐2‐azapurine (1) with 2‐deoxy‐3,5‐di‐ O ‐(p‐toluoyl)‐α‐ D ‐erythro‐pentofuranosyl chloride (2) yields the 2′‐deoxy‐β‐ D ‐ribofuranosides 3 – 5 stereoselectively. The distribution of regioisomers is as follows: N‐9 (32%); N‐2 (30%), and N‐7 (7%) together with a minor amount of an unidentified labile glycosylation product. The anomeric configuration and the site of glycosylation have been assigned on the basis of the 1 H‐NOE difference spectral data in combination with gated‐decoupled 13 C‐NMR and selective INEPT spectroscopy. The regioisomeric 6‐methylthio nucleosides have been converted into 6‐substituted derivatives of biological interest including 2′‐deoxy‐2‐azaadenosine (8) . Compound 8 is a substrate of adenosine deaminase.