PM3 study of cyclization of α-and β-D-glucosyl azides into 1,2-cyclic carbamates

P. Friant-Michel, A. Marsura, J. Kovacs, I. Pintér, J. L. Rivail

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The reaction of azido sugars with triphenylphosphine and carbon dioxide leading to cyclic carbamates has been studied by means of PM3 semiempirical quantum chemical computations to elucidate the detailed mechanisms of chemical processes involved in this transformation. Our results clearly indicate that the mechanism involving an isocyanate intermediate is preferred for both α-and β-anomers. In addition, we find that, in the case of the α-anomer, steric hindrance prevents the occurrence of direct cyclization and requires the opening of the pyranose ring, in contrast to the case of the β-anomer. This result explains the poor yield and the occurrence of three isomeric cyclic carbamates when the reaction is performed on the α-anomer.

Original languageEnglish
Pages (from-to)61-69
Number of pages9
JournalJournal of Molecular Structure: THEOCHEM
Volume395-396
Issue number1-3
DOIs
Publication statusPublished - May 26 1997

Keywords

  • Amino sugars
  • Cyclic carbamates
  • Iminophosphoranes
  • PM3 study

ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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