title: Chemoselective activation of nucleoside 3'-O-methylphosphonothioates with 1,3,5-triazinyl morpholinium salts.
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.
authors.affiliation: 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
authors.forename: Lucyna A
authors.initials: LA
authors.lastname: Wozniak
authors.forename: Marcin
authors.initials: M
authors.lastname: Góra
authors.forename: Wojciech J
authors.initials: WJ
authors.lastname: Stec
mesh_terms: 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
chemical_list: D009025:Morpholines; D009705:Nucleosides; D009946:Organothiophosphorus Compounds; D012492:Salts