Studies into the preparation of 1-deoxy-1-thiocyanato-D-glycopyranosyl cyanides and the anomeric effect of the thiocyanate group

László Somsák, Katalin Czifrák, Tamás Deim, László Szilágyi, Attila Bényei

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10 Citations (Scopus)

Abstract

The reaction of per-O-acetylated 1-bromo-1-deoxy-α-D-arabinopyranosyl cyanide with thiocyanate ions gave the corresponding 1-deoxy-1-thiocyanato-α- and β-D-arabinopyranosyl cyanides. In the reaction of the per-O-acetylated 1-bromo-1-deoxy-β-D-xylopyranosyl cyanide and its per-O-benzoylated β-D-glucopyranosyl analogue the corresponding 2-hydroxy-glycal esters formed in addition to the anomeric pair of thiocyanato-cyanides. The formation of 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl thiocyanate was demonstrated in the reaction of benzobromoglucose with thiocyanate ions. The equilibrium constant between 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thiocyanato-α- and β-D-galactopyranosyl cyanides was determined. Based on this value, the equilibrium ratio for the 2,3,4,6-tetra-O-acetyl-α- and β-D-galactopyranosyl thiocyanates was calculated to be 94:6, and the anomeric effect of the SCN group was estimated to exceed 3 kcal/mol. X-Ray crystallographic data support endo- and exo-anomeric effects of the SCN moiety.

Original languageEnglish
Pages (from-to)731-736
Number of pages6
JournalTetrahedron Asymmetry
Volume12
Issue number5
DOIs
Publication statusPublished - Apr 2 2001

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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