First synthesis of biopterin α-D-glucoside

Tadashi Hanaya, Hiroki Baba, Hiroshi Yamamoto

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

A novel glycosyl donor, 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)-α- D-glucopyranosy bromide (15) was efficiently prepared from D-glucose in 8 steps. The first synthesis of 2'-O-(α-D-glucopyranosyl)biopterin (2) was achieved by treatment of the key precursor, N2-(N,N- dimethylaminomethylene)-1'-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl] biopterin (6) with 15 in the presence of silver triflate and tetramethylurea, followed by removal of the protecting groups.

Original languageEnglish
Pages (from-to)747-753
Number of pages7
JournalHeterocycles
Volume77
Issue number2
DOIs
Publication statusPublished - Feb 1 2009

Fingerprint

Biopterin
Glucosides
Bromides
Glucose

Keywords

  • Biopterine d-Glucoside
  • Protecting Group
  • Pteridine
  • Pterine Glycoside
  • Selective α-Glycosylation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Pharmacology

Cite this

First synthesis of biopterin α-D-glucoside. / Hanaya, Tadashi; Baba, Hiroki; Yamamoto, Hiroshi.

In: Heterocycles, Vol. 77, No. 2, 01.02.2009, p. 747-753.

Research output: Contribution to journalArticle

Hanaya, Tadashi ; Baba, Hiroki ; Yamamoto, Hiroshi. / First synthesis of biopterin α-D-glucoside. In: Heterocycles. 2009 ; Vol. 77, No. 2. pp. 747-753.
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