Action of toluene-p-thiol and triethylamine on fully protected thymidylyl-(3′→ 5′)-thymidine. Possible occurrence of thiolate ion-promoted internucleotide cleavage in the synthesis of oligonucleotides by the phosphotriester approach
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 9,p. 2451-2455
- https://doi.org/10.1039/p19810002451
Abstract
When 5′-O-methoxytetrahydropyranylthymidylyl-(3′→ 5′)-3′-O-methoxytetrahydropyranylthymidine o-chlorophenyl ester (12) is treated with an excess of toluene-p-thiol and triethylamine in acetonitrile solution at room temperature, it is cleaved to give 5′-O-methoxytetrahydropyranylthymidine 3′-(o-chlorophenyl) phosphate (10) and 5′-deoxy-5′-(p-tolylthio)-3′-O-methoxytetrahydropyranylthymidine(13). The bearing of this result on the synthesis of oligonucleotides by the phosphotriester approach is discussed.This publication has 2 references indexed in Scilit:
- 4-Nitrophenyl phenyl phosphorochloridate: a new phosphorylating agent for oligonucleotide synthesisJournal of the Chemical Society, Chemical Communications, 1977
- The phosphotriester approach to oligonucleotide synthesis: preparation of oligo- and poly-thymidylic acidsJournal of the Chemical Society, Perkin Transactions 1, 1977