Efficient total syntheses of natural pterin glycosides: limipterin and tepidopterin

Tadashi Hanaya, Hiroki Baba, Hiroki Toyota, Hiroshi Yamamoto

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The key, versatile precursors N2-(N,N-dimethylaminomethylene)-1′-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]biopterin (29a) and its ciliapterin analog (29b) were prepared, respectively, from d-xylose (in 14 steps) and l-xylose (in 11 steps). Treatment of 29a and 29b with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl bromide in the presence of silver triflate and tetramethylurea, followed by removal of the protecting groups, led to the first selective syntheses of limipterin (3) and tepidopterin (5), respectively.

Original languageEnglish
Pages (from-to)2090-2100
Number of pages11
JournalTetrahedron
Volume64
Issue number9
DOIs
Publication statusPublished - Feb 25 2008

Fingerprint

Pterins
Xylose
Glycosides
Biopterin
Bromides
tepidopterin
trifluoromethanesulfonic acid
4-nitrophenyl
1,1,3,3-tetramethylurea

Keywords

  • Glycosylation
  • Protecting group
  • Pteridine
  • Pterin glycoside

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Efficient total syntheses of natural pterin glycosides : limipterin and tepidopterin. / Hanaya, Tadashi; Baba, Hiroki; Toyota, Hiroki; Yamamoto, Hiroshi.

In: Tetrahedron, Vol. 64, No. 9, 25.02.2008, p. 2090-2100.

Research output: Contribution to journalArticle

Hanaya, Tadashi ; Baba, Hiroki ; Toyota, Hiroki ; Yamamoto, Hiroshi. / Efficient total syntheses of natural pterin glycosides : limipterin and tepidopterin. In: Tetrahedron. 2008 ; Vol. 64, No. 9. pp. 2090-2100.
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