Transformation of aldoses into glycosylamine 1,2-(cyclic carbamates) (glyco-oxazolidin-2-ones) by reaction with potassium cyanate

J. Kovács, I. Pintér, Ursula Lendering, Peter Köll

Research output: Article

29 Citations (Scopus)

Abstract

Treatment of pentoses and some hexoses with potassium cyanate in aqueous solutions, buffered with sodium dihydrogen phosphate or ammonium chloride, gave glycosylamine 1,2-(cyclic carbamates) {glycofurano(or pyrano)[1,2-d]oxazolidin-2-ones}. Most of the products had furanoid structures, but d-mannose and d-lyxose gave preponderantly pyranose derivatives. Epimerisation at C-2 was observed in certain reactions. The products and their acetylated derivatives were characterised by 1H- and 13C-n.m.r. spectroscopy.

Original languageEnglish
Pages (from-to)155-166
Number of pages12
JournalCarbohydrate Research
Volume210
Issue numberC
DOIs
Publication statusPublished - márc. 20 1991

Fingerprint

Oxazolidinones
Pentoses
Ammonium Chloride
Hexoses
Carbamates
Mannose
Spectrum Analysis
Derivatives
Spectroscopy
sodium phosphate
potassium cyanate
lyxose

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

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abstract = "Treatment of pentoses and some hexoses with potassium cyanate in aqueous solutions, buffered with sodium dihydrogen phosphate or ammonium chloride, gave glycosylamine 1,2-(cyclic carbamates) {glycofurano(or pyrano)[1,2-d]oxazolidin-2-ones}. Most of the products had furanoid structures, but d-mannose and d-lyxose gave preponderantly pyranose derivatives. Epimerisation at C-2 was observed in certain reactions. The products and their acetylated derivatives were characterised by 1H- and 13C-n.m.r. spectroscopy.",
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T1 - Transformation of aldoses into glycosylamine 1,2-(cyclic carbamates) (glyco-oxazolidin-2-ones) by reaction with potassium cyanate

AU - Kovács, J.

AU - Pintér, I.

AU - Lendering, Ursula

AU - Köll, Peter

PY - 1991/3/20

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N2 - Treatment of pentoses and some hexoses with potassium cyanate in aqueous solutions, buffered with sodium dihydrogen phosphate or ammonium chloride, gave glycosylamine 1,2-(cyclic carbamates) {glycofurano(or pyrano)[1,2-d]oxazolidin-2-ones}. Most of the products had furanoid structures, but d-mannose and d-lyxose gave preponderantly pyranose derivatives. Epimerisation at C-2 was observed in certain reactions. The products and their acetylated derivatives were characterised by 1H- and 13C-n.m.r. spectroscopy.

AB - Treatment of pentoses and some hexoses with potassium cyanate in aqueous solutions, buffered with sodium dihydrogen phosphate or ammonium chloride, gave glycosylamine 1,2-(cyclic carbamates) {glycofurano(or pyrano)[1,2-d]oxazolidin-2-ones}. Most of the products had furanoid structures, but d-mannose and d-lyxose gave preponderantly pyranose derivatives. Epimerisation at C-2 was observed in certain reactions. The products and their acetylated derivatives were characterised by 1H- and 13C-n.m.r. spectroscopy.

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