Novel preparation of a 2′-O-acetyl-1′-O-(4-methoxybenzyl)-L- biopterin derivative, a versatile precursor for a selective synthesis of L-biopterin glycosides

Tadashi Hanaya, Hiroki Toyota, Hiroshi Yamamoto

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

L-Rhamnose was converted, over a 13-step-sequence, into 2′-O-acetyl-N2-(N,N-dimethylaminomethylene)-1′-O-(4- methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]-L-biopterin, an appropriately protected precursor of 1′-O- and 2′-O-monoglycosyl-L-biopterin. Thus, the first selective synthesis of these L-biopterin glycosides was accomplished by treatment of the precursor with either DDQ or sodium methoxide, then with tetra-O-benzoyl-α-D-glucopyranosyl bromide in the presence of silver triflate and tetramethylurea, followed by removal of the remaining protecting groups.

Original languageEnglish
Pages (from-to)2075-2078
Number of pages4
JournalSynlett
Issue number13
DOIs
Publication statusPublished - Aug 17 2006

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Keywords

  • Glycosylations
  • L-biopterin glycosides
  • Limipterin
  • Protecting groups
  • Pteridine

ASJC Scopus subject areas

  • Organic Chemistry

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