Synthetic studies on pterin glycosides: the first synthesis of 2′-O-(α-d-glucopyranosyl)biopterin

Tadashi Hanaya, Hiroki Baba, Hiroki Toyota, Hiroshi Yamamoto

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

l-Rhamnose was led, in a 14-step-sequence, to N2-(N,N-dimethylaminomethylene)-1′-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]biopterin (23), an appropriately protected precursor for 2′-O-glycosylation, while 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)-α-d-glucopyranosyl bromide (32), a novel glycosyl donor, was efficiently prepared from d-glucose in 8 steps. The first synthesis of 2′-O-(α-d-glucopyranosyl)biopterin (2a) was achieved by treatment of the key intermediate 23 with 32 in the presence of silver triflate and tetramethylurea, followed by successive removal of the protecting groups.

Original languageEnglish
Pages (from-to)7989-7997
Number of pages9
JournalTetrahedron
Volume65
Issue number38
DOIs
Publication statusPublished - Sep 19 2009

Keywords

  • Glycosylation
  • Protecting group
  • Pteridine
  • Pterin glycoside
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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