Chemoselective activation of nucleoside 3'-O-methylphosphonothioates with 1,3,5-triazinyl morpholinium salts |
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Authors: | Wozniak Lucyna A Góra Marcin Stec Wojciech J |
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Institution: | Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Bioorganic Chemistry, 112 Sienkiewicza Str., 90-363 Lodz, Poland. lwozniak@achilles.wam.lodz.pl |
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Abstract: | Chemoselective and stereospecific O-activation of 2'-deoxynucleoside 3'-O-methylphosphonothioates 5 with N-methyl-N-4,6-dimethoxy-1,3,5-triazin-2-yl morpholinium salts results in formation with retention of configuration of 5'-O-DMT-2'-deoxynucleoside 3'-O-(4,6 dimethoxy-1,3,5-triazin-2-yl methylphosphonothioates (7). Active esters 7 are convenient intermediates for hydrolytic interconversion of RP-5 into SP-5 and can be used as monomers for stereoselective synthesis of dinucleoside (3',5')-methyl phosphonothioates. |
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