Tetrahedron: Asymmetry

A convenient access to the 1, 5-anhydro forms of d-tagatose, l-rhamnulose and d-xylulose via 2-hydroxyglycal esters

P Jarglis, V Göckel, FW Lichtenthaler

Index: Jarglis, Pan; Goeckel, Volker; Lichtenthaler, Frieder W. Tetrahedron Asymmetry, 2009 , vol. 20, # 6-8 p. 952 - 960

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Citation Number: 8

Abstract

Zemplén methanolysis or a three-step protocol comprising hydroxylaminolysis, de-O- acetylation and deoximination smoothly and efficiently convert the benzoylated 2-hydroxy-d- glycals of d-galactose, l-rhamnose and d-xylose into their configurationally related 1, 5- anhydro-ketoses, thereby providing convenient access to the 1, 5-anhydro forms of d- tagatose, l-rhamnulose and d-xylulose. Invariably obtained as amorphous solids, they are ...