Tetra-n-propylammonium tetra-oxoruthenate(VII): a reagent of choice for the oxidation of diversely protected glycopyranoses and glycofuranoses to lactones

2,3,4,6-Tetra-O-benzyl-d-glucopyranose, 2,3,5-tri-O-allyl-d-ribofuranose, 2,3,5-tri-O-allyl- and -tri-O-benzyl-d-arabinofuranose, and 2-deoxy-3,5-di-O-allyl-d-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-d-arabino-hexono-1,5-lactone (14) from 3,4,6-tri-O-benzyl-1,5-anhydro-2-deoxy-d-arabino-hex-1 enitol (65% overall yield) is described.