Transformation of d-allose and l-gulose with potassium cyanate into cyclic carbamates

József Kovács, István Pintér, Dirk Abeln, Jürgen Kopf, Peter Köll

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Treatment of d-allose and l-gulose with potassium cyanate in aqueous solutions, buffered with sodium dihydrogen phosphate, gave cyclic carbamates (N,O-carbonyl derivatives) of the derived glycosylamines. d-Allose gave the furanoid 1,2-cis-carbamate as a single product, but l-gulose yielded a complex mixture of the furanoid 1,2-cis-carbamate, the pyranoid 1,2- and 1,3-cis-carbamates, and the furanoid 1,2-cis-carbamate of β-l-ido configuration as a product of epimerization at C-2. The structures were derived from the NMR spectra of the free compounds and those of their acetates. The structure of the main product in the reaction of l-gulose, that of the pyranoid 1,2-cis-carbamate, was proved independently by X-ray structure determination of the tetra-acetate. The pyranoid ring was found to exist in the OT2(l) conformation.

Original languageEnglish
Pages (from-to)97-106
Number of pages10
JournalCarbohydrate Research
Volume257
Issue number1
DOIs
Publication statusPublished - Apr 16 1994

    Fingerprint

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Cite this