Nucleoside <i>H</i>-Phosphonates. 18. Synthesis of Unprotected
Nucleoside 5‘-<i>H</i>-Phosphonates and Nucleoside
5‘-<i>H</i>-Phosphonothioates and Their Conversion into the
5‘-Phosphorothioate and 5‘-Phosphorodithioate Monoesters
Jadwiga Jankowska
Anna Sobkowska
Jacek Cieślak
Michał Sobkowski
Adam Kraszewski
Jacek Stawiński
David Shugar
10.1021/jo980491u.s001
https://acs.figshare.com/articles/journal_contribution/Nucleoside_i_H_i_-Phosphonates_18_Synthesis_of_Unprotected_Nucleoside_5_-_i_H_i_-Phosphonates_and_Nucleoside_5_-_i_H_i_-Phosphonothioates_and_Their_Conversion_into_the_5_-Phosphorothioate_and_5_-Phosphorodithioate_Monoesters/3712113
A simple and efficient protocol for the preparation of unprotected nucleoside 5‘-<i>H</i>-phosphonates
and nucleoside 5‘-<i>H</i>-phosphonothioates via a one-step deprotection of suitable precursors with
methylamine has been developed. The synthetic utility of the unprotected nucleotide derivatives
was demonstrated by converting them under mild conditions to the corresponding nucleoside 5‘-phosphorothioate and nucleoside 5‘-phosphorodithioate monoesters. Factors affecting oxidation of
<i>H</i>-phosphonate, <i>H</i>-phosphonothioate, and phosphite derivatives with elemental sulfur are also
discussed.
1998-10-28 00:00:00
phosphonate
nucleotide derivatives
phosphonothioate
Nucleoside H
nucleoside
Phosphonate
18. Synthesis
phosphite derivatives