Synthesis and rearrangement of 3 '-alpha-diethylphosphono-3 '-beta-O-methanesulfonyluridines

Citation
Tj. Baker et Df. Wiemer, Synthesis and rearrangement of 3 '-alpha-diethylphosphono-3 '-beta-O-methanesulfonyluridines, TETRAHEDRON, 56(20), 2000, pp. 3127-3131
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
20
Year of publication
2000
Pages
3127 - 3131
Database
ISI
SICI code
0040-4020(20000512)56:20<3127:SARO3'>2.0.ZU;2-X
Abstract
Preparation of a uridine derivative bearing both diethylphosphono and metha nesulfonate substituents at the 3'-position has been accomplished by reacti on of the corresponding alpha-hydroxy phosphonate with methanesulfinyl chlo ride and subsequent oxidation. While this methanesulfonate did not undergo elimination under standard reaction conditions, treatment with TBAF results in a novel rearrangement leading to the corresponding 2'-phosphate. (C) 20 00 Elsevier Science Ltd. All rights reserved.