DMSO-Oxalyl Chloride for the Oxidation of Carbohydrates

DMSO-Oxalyl Chloride에 의한 당의 산화

DMSO-oxalyl chloride at low temperature in methylene chloride reacted with isolated secondary hydroxyl groups in some monosaccharides to give alkoxysulfonium salts, convertible to carbonyls in high yields upon addition of triethylamine. And 1, 2:5, 6-di-O-isopropylidene-.alpha.- D-allofuranose which is the key intermediate in the synthesis of 3-O-acetyl-5-O-benzoyl- 2-deoxy-2- fluoro-D-arabinofuranosyl bromide, was also obtained by oxidizing 1, 2:5, 6-di-O-isopropylidene-.alpha.- D-glucofuranose with the oxidizing reagent, followed by reduction with sodium borohydride.