The synthesis of 3-acetamido-2,3,5,6-tetradeoxy-5-fluoro-d,l-ribo-hexofuranose by the direct fluorination of methyl 3-acetamido-2,3,6-trideoxy-d,l-arabino-hexopyranoside (methyl N-acetyl-d,l-acosaminide)

John T. Welch, Britt Marie Svahn, Seetha Eswarakrishnan, John P. Hutchinson, Jon Zubieta

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

3-Acetamido-2,3,5,6-tetradeoxy-5-fluoro-d,l-ribo-hexofuranose was synthesized by direct, fluorinative dehydroxylation of methyl 3-acetamido-2,3,6-trideoxy-d,l-arabino-hexopyranoside with sulfur tetrafluoride-hydrogen fluoride. The furanose form and the ribo configuration, indicated by 13C- and 1H-n.m.r. spectroscopy, respectively, were confirmed by a single-crystal, X-ray diffraction study.

Original languageEnglish (US)
Pages (from-to)221-231
Number of pages11
JournalCarbohydrate Research
Volume132
Issue number2
DOIs
StatePublished - Sep 15 1984
Externally publishedYes

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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