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

J. Kovács, I. Pintér, Dirk Abeln, Jürgen Kopf, Peter Köll

Research output: Article

12 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 - ápr. 16 1994

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Carbamates
Acetates
Complex Mixtures
Conformations
gulose
allose
potassium cyanate
Nuclear magnetic resonance
X-Rays
Derivatives
X rays

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Transformation of d-allose and l-gulose with potassium cyanate into cyclic carbamates. / Kovács, J.; Pintér, I.; Abeln, Dirk; Kopf, Jürgen; Köll, Peter.

In: Carbohydrate Research, Vol. 257, No. 1, 16.04.1994, p. 97-106.

Research output: Article

Kovács, J. ; Pintér, I. ; Abeln, Dirk ; Kopf, Jürgen ; Köll, Peter. / Transformation of d-allose and l-gulose with potassium cyanate into cyclic carbamates. In: Carbohydrate Research. 1994 ; Vol. 257, No. 1. pp. 97-106.
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N2 - 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.

AB - 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.

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