Synthesis and separation of diastereomers of uridine 2',3'-cyclic boranophosphate

Bioorg Med Chem Lett. 2001 Mar 12;11(5):615-7. doi: 10.1016/s0960-894x(00)00700-9.

Abstract

The first boron-containing 2',3'-cyclic phosphate-modified analogue, uridine 2',3'-cyclic boranophosphate (2',3'-cyclic-UMPB), was synthesized. 5'-O-Protected uridine was cyclophosphorylated by diphenyl H-phosphonate to yield uridine 2',3'-cyclic H-phosphonate, which upon silylation followed by boronation and subsequent acid treatment gave 2',3'-cyclic-UMPB in high yield. The two diastereomers of 2',3'-cyclic-UMPB were separated by HPLC. An alternative method for synthesis of uridine 2',3'-cyclic phosphorothioate (2',3'-cyclic-UMPS) via H-phosphonate was also described.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Boron Compounds / chemical synthesis*
  • Boron Compounds / chemistry*
  • Boron Compounds / isolation & purification
  • Chromatography, High Pressure Liquid
  • Molecular Conformation
  • Molecular Structure
  • Ribonucleases / antagonists & inhibitors
  • Stereoisomerism
  • Uridine / analogs & derivatives
  • Uridine / chemical synthesis*
  • Uridine / chemistry*
  • Uridine / isolation & purification

Substances

  • Boron Compounds
  • uridine-2',3'-cyclic boranophosphate
  • Ribonucleases
  • Uridine