91837-36-4Relevant articles and documents
Stereochemistry of internucleotide bond formation by the H-phosphonate method. 7. Stereoselective formation of ribonucleoside (RP)- and (SP)-3′-H-phosphonothioate monoesters
Sobkowski, Michal,Stawinski, Jacek,Kraszewski, Adam
experimental part, p. 410 - 419 (2010/07/04)
Ribonucleoside 3′-H-phosphonothioate monoesters exist in the form of (RP)- and (SP)-diastereomers. In order to obtain them in good yields and in high stereochemical purity, stereoselective strategies for their preparation were investigated. For the synthesis of the (RP)-isomer, a stereoselective sulfhydrolysis of an activated nucleoside H-phosphonate was developed, while the monoesters with an (SP)-configuration were prepared by asymmetric transformation of diastereomeric mixtures of nucleoside 3′-H-phosphonothioates using either a condensation with 9-fluorenemethanol, followed by β-elimination, or via pivaloylation-hydrolysis reaction sequence. A tentative assignment of the absolute configurations of the obtained diastereomers of 3′-H-phosphonothioate esters was carried out via a stereochemical correlation analysis.
3-H-2,1-benzoxathiol-3-one 1-oxide - A new reagent for stereospecific oxidation of nucleoside H-phosphonothioate diesters
Stawinski, Jacek,Thelin, Mats
, p. 3189 - 3192 (2007/10/02)
Oxidation of diastereomerically pure nucleoside H-phosphonothioate diesters with 3-H-2,1-benzoxathiol-3-one 1-oxide (1) was found to be stereospecific and occurred with retention of configuration. Absolute configurations of diribonucleoside H-phosphonothioate diastereomers were established via stereochemical correlation using m-chloroperoxybenzoic acid for stereospecific conversion of ribonucleoside H-phosphonothioate to the corresponding H-phosphonate diesters.
The automated synthesis of sulfur-containing oligodeoxyribonucleotides using 3H-1,2-benzodithiol-3-one 1,1-dioxide as a sulfur-transfer reagent
Iyer,Phillips,Egan,Regan,Beaucage
, p. 4693 - 4699 (2007/10/02)
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