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

Journal Article (Journal Article)

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.

Full Text

Duke Authors

Cited Authors

  • He, K; Shaw, BR

Published Date

  • March 2001

Published In

Volume / Issue

  • 11 / 5

Start / End Page

  • 615 - 617

PubMed ID

  • 11266154

Electronic International Standard Serial Number (EISSN)

  • 1464-3405

International Standard Serial Number (ISSN)

  • 0960-894X

Digital Object Identifier (DOI)

  • 10.1016/s0960-894x(00)00700-9


  • eng