An efficient synthesis of 2′-O-(β-d-glucopyranosyl)- and 2′-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-biopterins

Tadashi Hanaya, Kazuyuki Soranaka, Koichiro Harada, Hiroshi Yamaguchi, Ryo Suzuki, Yusumi Endo, Hiroshi Yamamoto, Wolfgang Pfleiderer

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

N2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1′,2′-di-O-trimethylsilyl-L-biopterin (6) was prepared from L-biopterin in 5 steps. Glycosylation of 6 with 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate (9) and 1,3,4,6-tetra-O-acetyl-2-phtalimido-β-D-glucopyranose (10) respectively afforded the corresponding 2′-O-(β-D-glucopyranosyl) derivatives (12b, 12c) as major products. Removal of protecting groups of 12c provided naturally occurring limipterin (2).

Original languageEnglish
Pages (from-to)299-310
Number of pages12
JournalHeterocycles
Volume67
Issue number1
DOIs
Publication statusPublished - Jan 1 2006

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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    Hanaya, T., Soranaka, K., Harada, K., Yamaguchi, H., Suzuki, R., Endo, Y., Yamamoto, H., & Pfleiderer, W. (2006). An efficient synthesis of 2′-O-(β-d-glucopyranosyl)- and 2′-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-biopterins. Heterocycles, 67(1), 299-310. https://doi.org/10.3987/COM-05-S(T)28