The synthesis of dithymidine boranophosphate by the oxathiaphospholane approach.
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.
Okruszek
A
A
Department of Bioorganic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Lódź, Poland. okruszek@bio.cbmm.lodz.pl
Sierzchała
A
A
Zmudzka
K
K
Stec
W J
WJ
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*
D001896:Boron Compounds; D009711:Nucleotides; D010710:Phosphates; C107859:dithymidine boranomonophosphate; C434797:oxathiaphospholane; D012266:Ribose; D013936:Thymidine