Synthesis of some derivatives of C-(1-deoxy-1-N-substituted-d- glucopyranosyl)formic acid (D-gluco-hept-2-ulopyranosonic acid) as potential inhibitors of glycogen phosphorylase

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Abstract

Per-O-benzoylated derivatives (amide, methyl ester and glycinamide) of C-(1-azido-1-deoxy-α-d-glucopyranosyl)formic acid obtained by azide substitution in the corresponding C-(1-bromo-1-deoxy-β-d-glucopyranosyl) formic acid derivatives were debenzoylated by the Zemplén-protocol. Per-O-benzoylated C-(1-azido-1-deoxy-α-d-glucopyranosyl)formamide was dehydrated by oxalyl chloride-DMF to give the corresponding nitrile, while from its reduction mixture obtained by Raney-nickel or sodium hydrogentelluride C-(1-amino-1-deoxy-β-d-glucopyranosyl)formamide could be isolated. Acetylation of this amino-amide by Ac2O/Py and subsequent debenzoylation gave C-(1-acetamido-1-deoxy-β-d-glucopyranosyl)formamide. Applying the same conditions to the crude reduction mixture allowed the α-anomer to be isolated as a minor component. An alternative pathway to produce the above β-anomer appeared in the reaction of C-(1-bromo-1-deoxy- β-d-glucopyranosyl)formamide with CH3CN in the presence of Ag2CO3 to yield 1-acetamido-2,3,4,6,-tetra-O-benzoyl-1- deoxy-β-d-glucopyranosyl cyanide, which was hydrated, in the presence of TiCl4, to the formamide. Some of the new compounds were shown to be weak inhibitors of muscle glycogen phosphorylase b.

Original languageEnglish
Pages (from-to)2328-2334
Number of pages7
JournalCarbohydrate Research
Volume340
Issue number14
DOIs
Publication statusPublished - Oct 17 2005

Keywords

  • Glycogen phosphorylase inhibitors
  • Glycosyl amides
  • Glycosyl azides
  • Hept-2-ulopyranosonic acid derivatives

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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