Diastereospecific chemical synthesis of ribonucleosides-3 ',4 ',5 ',5 ''-d(4)

Authors
Trifonova, A Foldesi, A Dinya, Z Chattopadhyaya, J
Citation
A. Trifonova et al., Diastereospecific chemical synthesis of ribonucleosides-3 ',4 ',5 ',5 ''-d(4), TETRAHEDRON, 55(15), 1999, pp. 4747-4762
Citations number
65
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
15
Year of publication
1999
Pages
4747 - 4762
Database
ISI
SICI code
0040-4020(19990409)55:15<4747:DCSOR'>2.0.ZU;2-L
Abstract
The diastereospecific chemical syntheses of uridine-3',4',5',5"-d(4), cylid ine-3',4',5',5''-d(4), adenosine-3',4',5',5"-d4 and guanosine-3',4',5',5"-d (4) (>97 atom % H-2 at C3', C4' and C5') have been achieved by condensation of appropriately protected aglycone with 1-O-acetyl 2,3,5-tri-O-(4-toluoyl )-alpha/beta-(D) under bar-ribofuranose-3,4,5,5'-d(4) (27), which has been obtained in an overall yield of 20 % in 11 steps starting from 50 mmol of 2 : 5,6- Di-O-isopropylidene-alpha-(D) under bar-glucose. (C) 1999 Elsevier S cience Ltd. All rights reserved.