Chemoselective activation of nucleoside 3'-O-methylphosphonothioates with 1,3,5-triazinyl morpholinium salts.
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.
Wozniak
Lucyna A
LA
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
Góra
Marcin
M
Stec
Wojciech J
WJ
D015394:Molecular Structure; D009025:Morpholines / Q000737:chemistry*; D009705:Nucleosides / Q000737:chemistry*; D009946:Organothiophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D012492:Salts / Q000737:chemistry; D013237:Stereoisomerism
D009025:Morpholines; D009705:Nucleosides; D009946:Organothiophosphorus Compounds; D012492:Salts