160056-41-7Relevant academic research and scientific papers
Studies on aryl H-phosphonates. I. An efficient method for the preparation of deoxyribo- and ribonucleoside 3'-H-phosphonate monoesters by transesterification of diphenyl H-phosphonate
Jankowska,Sobkowski,Stawinski,Kraszewski
, p. 3355 - 3358 (1994)
A convenient method for the preparation of deoxyribonucleoside and ribonucleoside 3'-H-phosphonate monoesters via transesterification of diphenyl H-phosphonate with suitable protected nucleosides in pyridine is described.
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.
