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

Publication ,  Journal Article
He, K; Shaw, BR
Published in: Bioorganic & medicinal chemistry letters
March 2001

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.

Duke Scholars

Published In

Bioorganic & medicinal chemistry letters

DOI

EISSN

1464-3405

ISSN

0960-894X

Publication Date

March 2001

Volume

11

Issue

5

Start / End Page

615 / 617

Related Subject Headings

  • Uridine
  • Stereoisomerism
  • Ribonucleases
  • Molecular Structure
  • Molecular Conformation
  • Medicinal & Biomolecular Chemistry
  • Chromatography, High Pressure Liquid
  • Boron Compounds
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
 

Citation

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MLA
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He, K., & Shaw, B. R. (2001). Synthesis and separation of diastereomers of uridine 2',3'-cyclic boranophosphate. Bioorganic & Medicinal Chemistry Letters, 11(5), 615–617. https://doi.org/10.1016/s0960-894x(00)00700-9
He, K., and B. R. Shaw. “Synthesis and separation of diastereomers of uridine 2',3'-cyclic boranophosphate.Bioorganic & Medicinal Chemistry Letters 11, no. 5 (March 2001): 615–17. https://doi.org/10.1016/s0960-894x(00)00700-9.
He K, Shaw BR. Synthesis and separation of diastereomers of uridine 2',3'-cyclic boranophosphate. Bioorganic & medicinal chemistry letters. 2001 Mar;11(5):615–7.
He, K., and B. R. Shaw. “Synthesis and separation of diastereomers of uridine 2',3'-cyclic boranophosphate.Bioorganic & Medicinal Chemistry Letters, vol. 11, no. 5, Mar. 2001, pp. 615–17. Epmc, doi:10.1016/s0960-894x(00)00700-9.
He K, Shaw BR. Synthesis and separation of diastereomers of uridine 2',3'-cyclic boranophosphate. Bioorganic & medicinal chemistry letters. 2001 Mar;11(5):615–617.
Journal cover image

Published In

Bioorganic & medicinal chemistry letters

DOI

EISSN

1464-3405

ISSN

0960-894X

Publication Date

March 2001

Volume

11

Issue

5

Start / End Page

615 / 617

Related Subject Headings

  • Uridine
  • Stereoisomerism
  • Ribonucleases
  • Molecular Structure
  • Molecular Conformation
  • Medicinal & Biomolecular Chemistry
  • Chromatography, High Pressure Liquid
  • Boron Compounds
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry