Reactivity of nucleoside 5 '-O-phosphates, 5 '-O-phosphorothioates, 5 '-O-methanephosphonates, and 5 '-O-methanephosphonothioates toward activated Xylonucleosides

Authors
Yang, XB Misiura, K Stec, WJ
Citation
Xb. Yang et al., Reactivity of nucleoside 5 '-O-phosphates, 5 '-O-phosphorothioates, 5 '-O-methanephosphonates, and 5 '-O-methanephosphonothioates toward activated Xylonucleosides, HETEROAT CH, 10(2), 1999, pp. 91-104
Citations number
32
Categorie Soggetti
Chemistry
Journal title
HETEROATOM CHEMISTRY
ISSN journal
10427163 → ACNP
Volume
10
Issue
2
Year of publication
1999
Pages
91 - 104
Database
ISI
SICI code
1042-7163(1999)10:2<91:RON5'5>2.0.ZU;2-8
Abstract
Alkylation of ambident thymidine 5'-O-(O-alkyl phosphorothioate) anions by means of 3'-O-sulfonylated xylothymidine occurs at both O- and S-nucleophil ic centers, and formation of an internucleotide bond is accompanied by the process of elimination. Lack of chemoselectivity and low yields of products discriminate against such an approach as an effective method of stereocont rolled synthesis of P-chiral oligo(nucleoside phosphorothioate)s. (C) 1999 John Wiley & Sons, Inc.