Institution: | Laboratoire de Chimie des Glucides, Université Pierre et Marie Curie, 4 Place Jussieu, 75005 Paris, France |
Abstract: | 2,3,4,6-Tetra-O-benzyl-
-glucopyranose, 2,3,5-tri-O-allyl-
-ribofuranose, 2,3,5-tri-O-allyl- and -tri-O-benzyl-
-arabinofuranose, and 2-deoxy-3,5-di-O-allyl-
-erythro-pentofuranose were oxidized to their corresponding lactones 6–10 by dimethyl sulfoxide activated by oxalyl chloride, pyridinium dichromate in the presence of molecular sieves and acetic acid, and tetra-n-propylammonium tetra-oxoruthenate(VII) using 4-methylmorpholine N-oxide as cooxidant. With the latter reagent, analytically pure lactones were obtained in 83–98% yield. A multistep preparation of 3,4,6-tri-O-benzyl-2-deoxy-
-arabino-hexono-1,5-lactone (14) from 3,4,6-tri-O-benzyl-1,5-anhydro-2-deoxy-
-arabino-hex-1 enitol (65% overall yield) is described. |