Synthesis of 6-hydroxymethylpterin α- And β-D-glucosides

Tadashi Hanaya, Hiroki Baba, Kazumasa Ejiri, Hiroshi Yamamoto

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The key precursor, N2-(N,N-dimethylaminomethylene)-6-hydroxy- methyl-3-[2-(4-nitrophenyl)ethyl]pterin (11) was efficiently prepared from 2,5,6-triamino-4-hydroxypyrimidine (8) in 5 steps. The first, unequivocal synthesis of 6-hydroxymethylpterin α-D-glucoside (6a) was achieved by treatment of 11 with 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)-α-D-gluco- pyranosyl bromide (16) in the presence of tetraethylammonium bromide and N-ethyldiisopropylamine, followed by removal of the protecting groups, while 6-hydroxymethylpterin β-D-glucoside (6b) was prepared by means of selective glycosylation of 11 with 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl bromide (12) in the presence of silver triflate and tetramethylurea.

Original languageEnglish
Pages (from-to)1013-1025
Number of pages13
JournalHeterocycles
Volume80
Issue number2
DOIs
Publication statusPublished - Mar 1 2010

Keywords

  • D-Glucopyranosyl Bromide
  • Protecting Group
  • Pteridine
  • Pterin Glycoside
  • Selective Glycosylation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis of 6-hydroxymethylpterin α- And β-D-glucosides'. Together they form a unique fingerprint.

  • Cite this