The synthesis of dithymidine boranophosphate by the oxathiaphospholane approach

Citation
A. Okruszek et al., The synthesis of dithymidine boranophosphate by the oxathiaphospholane approach, NUCLEOS NUC, 20(10-11), 2001, pp. 1843-1849
Citations number
16
Categorie Soggetti
Biochemistry & Biophysics
Journal title
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
ISSN journal
15257770 → ACNP
Volume
20
Issue
10-11
Year of publication
2001
Pages
1843 - 1849
Database
ISI
SICI code
1525-7770(2001)20:10-11<1843:TSODBB>2.0.ZU;2-9
Abstract
The application of the oxathiaphospholane approach for the synthesis of dit hymidine boranphospate was evaluated. It was shown, that although the nucle oside-3'-O-oxathiaphospholane-borane complexes 2 or 6 could not be chromato graphically separated into diastereomerically pure species due to their app arent instability to moisture, they can be successfully applied to the non- stereocontrolled formation of internucleotide boranophosphate bond by react ion with 5'-OH-nucleoside in the presence of DBU. Attempts to apply the rel ated dithiaphospholane approach for the preparation of dithymidine boranoph osphorothioate were unsuccessful.