title: The synthesis of dithymidine boranophosphate by the oxathiaphospholane approach.
abstract: The application of the oxathiaphospholane approach for the synthesis of dithymidine boranphospate was evaluated. It was shown, that although the nucleoside-3'-O-oxathiaphospholane-borane complexes 2 or 6 could not be chromatographically separated into diastereomerically pure species due to their apparent instability to moisture, they can be successfully applied to the non-stereocontrolled formation of internucleotide boranophosphate bond by reaction with 5'-OH-nucleoside in the presence of DBU. Attempts to apply the related dithiaphospholane approach for the preparation of dithymidine boranophosphorothioate were unsuccessful.
authors.affiliation: Department of Bioorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Lódź, Poland. okruszek@bio.cbmm.lodz.pl
authors.forename: A
authors.initials: A
authors.lastname: Okruszek
authors.forename: A
authors.initials: A
authors.lastname: Sierzchała
authors.forename: K
authors.initials: K
authors.lastname: Zmudzka
authors.forename: W J
authors.initials: WJ
authors.lastname: Stec
mesh_terms: D001896:Boron Compounds / Q000138:chemical synthesis*; D008956:Models, Chemical; D009711:Nucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry; D012266:Ribose / Q000031:analogs & derivatives* / Q000737:chemistry*; D013936:Thymidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
chemical_list: D001896:Boron Compounds; D009711:Nucleotides; D010710:Phosphates; C107859:dithymidine boranomonophosphate; C434797:oxathiaphospholane; D012266:Ribose; D013936:Thymidine