An efficient synthesis of 2′-O-(β-D-ribofuranosyl)biopterin

Tadashi Hanaya, Kiyoshi Torigoe, Kazuyuki Soranaka, Hiroshi Fujita, Hiroshi Yamamoto, Wolfgang Pfleiderer

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

N2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]- 1′,2′-di-O-(trimethylsilyl)biopterin (4) was prepared from biopterin (1a, 86% overall yield) in 5 steps. Glycosylation of 4 with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (5a) and its 2,3,5-tri-O-benzoyl analog (5b) respectively afforded the corresponding 2′-O-(2,3,5-tri-O- acetyl-and 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)biopterin derivatives (6a, 42% and 6b, 60%) as major products. Removal of the protecting groups of 6b provided 2′-O-(β-D-ribofuranosyl)biopterin (1c, 87% overall yield) in 3 steps.

Original languageEnglish
Pages (from-to)72-78
Number of pages7
JournalPteridines
Volume19
Issue number3
DOIs
Publication statusPublished - Sep 2008

Keywords

  • Biopterin D-riboside
  • Glycosylation
  • Protecting groups
  • Pterin glycoside

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Clinical Biochemistry

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  • Cite this

    Hanaya, T., Torigoe, K., Soranaka, K., Fujita, H., Yamamoto, H., & Pfleiderer, W. (2008). An efficient synthesis of 2′-O-(β-D-ribofuranosyl)biopterin. Pteridines, 19(3), 72-78. https://doi.org/10.1515/pteridines.2008.19.1.72