Perry Rosen

Synthesis of carbohydrate phostones as potential glycomimetics

A series of stereoisomeric monosaccharide °-phostones (cyclic phosphonate esters) were prepared and their structures were confirmed by single crystal X-ray analysis. Esterification of the D-gluco phostonic acid with appropriate sugar alcohols gave the first 1→6 and 1→4 disaccharide glycomimetics with phosphorus at the anomeric carbon of the non-reducing unit. Their structures and configuration at phosphorus were established by X-ray analysis.

Structural determination of ascorbic acid 2-o-phosphate formed via acid hydrolysis of an ascorbic acid 3-O-phosphinate

Abstract The synthesis and X-ray structural determination of 3-O-[(bis-morpholino)phosphinyl]-5,6-O-isopropylidene- l -ascorbate (9) are described. Acid-catalyzed hydrolysis of 9 afforded the 2-O-phosphate 6. Definitive structural proof of 6 is based on a study of the pH profile of its UV spectra as compared with those of ascorbic esters, 2 and 9 (Figs. 1–3).