Acyclic nucleoside analogues from thymine-substituted thymidines and related compounds

Citation
Am. Costa et al., Acyclic nucleoside analogues from thymine-substituted thymidines and related compounds, TETRAHEDRON, 55(21), 1999, pp. 6635-6642
Citations number
29
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
21
Year of publication
1999
Pages
6635 - 6642
Database
ISI
SICI code
0040-4020(19990521)55:21<6635:ANAFTT>2.0.ZU;2-E
Abstract
Hydrolysis of 3'-deoxy-3'-(thymin-1-yl)thymidine, 3'-deoxy-3'-(uracil-1-yl) thymidine, and related furanoses with two nucleobases has been investigated . 3'-beta-Substituted analogues, but not the 3'-alpha-substituted ones, aff ord isomeric pyranose nucleosides as intermediates, which have been isolate d (6c and 6d). Reduction of the hydrolysis products with sodium borohydride afford the corresponding acyclic compounds (2'-deoxy-D-ribitol or D-ribito l derivatives), which have been fully characterised as their peracetates. ( C) 1999 Elsevier Science Ltd. AII rights reserved.