First synthesis of tepidopterin [2′-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-threo-biopterin]

Tadashi Hanaya, Hiroki Baba, Hiroshi Yamamoto

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8 Citations (Scopus)

Abstract

N2-(N,N-Dimethylaminomethylene)-1′-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]-l-threo-biopterin (14) was prepared from l-xylose in an 11-step-sequence. The first synthesis of tepidopterin (3) was achieved by treatment of 14 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.

Original languageEnglish
Pages (from-to)2159-2162
Number of pages4
JournalCarbohydrate Research
Volume342
Issue number15
DOIs
Publication statusPublished - Nov 5 2007

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Keywords

  • Glycosylation
  • Pteridine
  • Pterin glycoside
  • Tepidopterin
  • l-threo-Biopterin

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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