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pubmed-article:9303190pubmed:abstractTextA new method of stereoselective preparation of di(2'-deoxy or 2'-OMe)ribonucleoside (3',5')-methanephosphonate 5 is presented. The DBU/LiCl-assisted reaction of 5'-O-DMT-(2'-deoxy or 2'-OMe)ribonucleoside 3'-O-(S-alkyl methanephosphonothioate) 9 with 5'-OH nucleosides proceeds with full stereospecificity, giving 5 in moderate to good yield. The conversion of 5'-O-DMT-(2'-deoxy or 2'-OMe) ribonucleoside 3'-methanephosphonoanilidothioates 8 and 3'-O-methanephosphonoanilidates 10 by means of NaH/CX2 (X = O,S) followed by S-alkylation leads to monomers 9, with the possibility of use of both separated diastereomers of 8 for the preparation of one selected diastereomer of 5. The relative configuration at the P atom in 2'-OMe and deoxynucleoside derivatives of compounds 9 was established by means of stereoselective degradation of nucleoside 3'-O-methanephosphonothioates 11 (precursors of 9) with nuclease P1.lld:pubmed
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pubmed-article:9303190pubmed:dateRevised2006-11-15lld:pubmed
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pubmed-article:9303190pubmed:articleTitleNovel cost-effective methanephosphonoanilidothioate approach to the stereoselective synthesis of dinucleoside (3',5')-methanephosphonates.lld:pubmed
pubmed-article:9303190pubmed:affiliationDepartment of Bioorganic Chemistry, Polish Academy of Sciences, Lód?, Poland.lld:pubmed
pubmed-article:9303190pubmed:publicationTypeJournal Articlelld:pubmed
pubmed-article:9303190pubmed:publicationTypeResearch Support, Non-U.S. Gov'tlld:pubmed