Total synthesis of pseudouridine: Via Heck-type C-glycosylation

Cheng Ping Yu, Hsin Yun Chang, Tun Cheng Chien

Research output: Contribution to journalArticle

Abstract

The reaction of 2,4-dimethoxy-5-iodopyrimidine (8) and 3,5-di-O-tert-butyldimethylsilyl protected ribofuranoid glycal 4 was carried out with Pd(OAc)2 as the catalyst, PPh3 as the ligand and Et3N as the base in DMF at 70 °C followed by desilylation to afford exclusively the β-anomer of 5-(2,3-dideoxy-3-oxoribofuranosyl)-2,4-dimethoxypyrimidine (11) in a very good yield. The subsequent protecting group and functional group interconversions furnished pseudouridine (Ψ, 1).

Original languageEnglish
Pages (from-to)8796-8803
Number of pages8
JournalNew Journal of Chemistry
Volume43
Issue number22
DOIs
Publication statusPublished - 2019 Jan 1

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Materials Chemistry

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