Efficient total syntheses of natural neopterin glycosides: Neopterin glucronide and solfapterin

Tadashi Hanaya, Katsuya Iwasaki, Kaori Saeki, Takafumi Hattori

Research output: Contribution to journalArticle

Abstract

1,2-Di-O-acetyl-N 2 -(N,N-dimethylaminomethylene)-3-[2-(4-nitrophenyl) ethyl]neopterin (11a) and its 1,2-di-O-benzoyl analog (11b) were prepared from neopterin in 5 steps, respectively. Glycosylation of 11a with methyl 2,3,4-tri-O-benzoylD-glucopyranosyluronate bromide (15b) in the presence of silver triflate afforded the corresponding 3'-O-(β-D-glucopyranosyl) neopterin derivative (18) in 64% yield. The similar treatment of 11b with 2-azido-3,4,6-tri-O-benzoyl-2-deoxy-a-D-glucopyranosyl bromide (21b) provided the corresponding 3'-O-(α-D-glucopyranosyl)neopterin derivative (23a) in 58% yield. The first syntheses of neopterin glucronide (5) and solfapterin (6) were achieved by successive removal of the protecting groups of 18 and 23a, respectively.

Original languageEnglish
Pages (from-to)390-409
Number of pages20
JournalHeterocycles
Volume95
Issue number1
DOIs
Publication statusPublished - Jan 1 2017

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Neopterin
Glycosides
Bromides
Derivatives
Glycosylation
solfapterin

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

Efficient total syntheses of natural neopterin glycosides : Neopterin glucronide and solfapterin. / Hanaya, Tadashi; Iwasaki, Katsuya; Saeki, Kaori; Hattori, Takafumi.

In: Heterocycles, Vol. 95, No. 1, 01.01.2017, p. 390-409.

Research output: Contribution to journalArticle

Hanaya, Tadashi ; Iwasaki, Katsuya ; Saeki, Kaori ; Hattori, Takafumi. / Efficient total syntheses of natural neopterin glycosides : Neopterin glucronide and solfapterin. In: Heterocycles. 2017 ; Vol. 95, No. 1. pp. 390-409.
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