A NOVEL METHOD FOR DEUTERATION OF 2'-DEOXY-4'-THIONUCLEOSIDES

Authors
MACCULLOCH AC WALKER RT
Citation
Ac. Macculloch et Rt. Walker, A NOVEL METHOD FOR DEUTERATION OF 2'-DEOXY-4'-THIONUCLEOSIDES, Tetrahedron, 54(41), 1998, pp. 12457-12464
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
41
Year of publication
1998
Pages
12457 - 12464
Database
ISI
SICI code
0040-4020(1998)54:41<12457:ANMFDO>2.0.ZU;2-2
Abstract
Oxidation of 2'-deoxy-5-ethyl-4'-thiouridine with sodium meta-periodat e yielded a separable mixture of (R) and(S)-sulfoxides. The structure of the (R)-sulfoxide was confirmed by X-ray analysis. When treated wit h sodium deuteroxide, the H-4' proton was exchanged for deuterium with epimerisation at C-4'. Treatment of the deuteriated sulfoxide nucleos ide with TFA/TMSBr furnished the starting material with H-4' replaced by deuterium. (C) 1998 Elsevier Science Ltd. All rights reserved.