Aryl H-phosphonates. 12. Synthetic and P-31 NMR studies on the preparationof nucleoside H-phosphonothioate and nucleoside H-phosphonodithioate monoesters

Citation
J. Cieslak et al., Aryl H-phosphonates. 12. Synthetic and P-31 NMR studies on the preparationof nucleoside H-phosphonothioate and nucleoside H-phosphonodithioate monoesters, J ORG CHEM, 65(21), 2000, pp. 7049-7054
Citations number
37
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
21
Year of publication
2000
Pages
7049 - 7054
Database
ISI
SICI code
0022-3263(20001020)65:21<7049:AH1SAP>2.0.ZU;2-D
Abstract
Transformation of nucleoside H-phosphonate monoesters into the correspondin g H-phosphonothioate and X-phosphonodithioate derivatives and possible side -reactions that may accompany this process were studied using P-31 NMR spec troscopy. These provided new insight into a possible mechanism involved in this transformation and constituted the basis for development of efficient methods for the preparation of nucleoside H-phosphonothioate and nucleoside H-phosphonodithioate monoesters using readily available H-phosphonate mono esters as starting materials.