Formation of 3-hexuloses in aldol reactions, analysis of the products as their O-isopropylidene derivatives by GC-MS.
A method for analysis of mixtures of 3-hexuloses by gas chromatography mass spectrometry of their di-O-isopropylidene derivatives has been elaborated. The origin of characteristic fragment ions in the mass spectra is suggested on the basis of the spectra of d(12) analogues, obtained by acetonation with acetone-d(6) and on MS/MS investigations. The method has been applied to product mixtures from aldol reactions between glycero-tetrulose and glycolaldehyde and between 2-pentuloses and formaldehyde. An interesting result is the formation of ribo-3-hexulose with a high degree of stereoselectivity in alkali catalysed reaction between erythro-2-pentulose and formaldehyde.
Ekeberg
Dag
D
Department of Chemistry, Biotechnology and Food Science, Section Chemistry, Agricultural University of Norway, PO Box 5003, N-1432 As, Norway.
Morgenlie
Svein
S
D000475:Alkenes; D002236:Carbohydrate Conformation; D008401:Gas Chromatography-Mass Spectrometry; D006601:Hexoses / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D013058:Mass Spectrometry; D008958:Models, Molecular
D000475:Alkenes; D006601:Hexoses; D007202:Indicators and Reagents; C013658:propylene