Nucleoside hydrogenphosphonates. Part 6. Reaction of nucleoside hydrogenphosphonates with arenesulphonyl chlorides
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 9,p. 1209-1214
- https://doi.org/10.1039/p29870001209
Abstract
The reaction of nucleoside 3′-hydrogenphosphonates (1) with 2,4,6-tri-isopropylbenzenesulphonyl chloride (TPS-Cl) in pyridine has been studied using 31P n.m.r. spectroscopy, and a general scheme for transformations occurring during this activation process is proposed. It was found that the reaction proceeded through several intermediates affording, as final products, the pyridine adduct of nucleoside 3′-metaphosphate (7), P1P2-bis-(S-aryl nucleosid-3′-yl) pyrophosphate (11a), and nucleoside S-aryl 3′-phosphorochloridate (13a), which upon addition of water were converted into nucleoside 3′-phosphate (2), P1P2-bis-(nucleosid-3′-yl) pyrophosphate (3), and nucleoside S-aryl 3′-phosphorothioate (4a).Keywords
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