A facile method for oxidation of primary alcohols to carboxylic acids and its application in glycosaminoglycan syntheses.
A convenient two-step, one-pot procedure was developed for the conversion of primary alcohols to carboxylic acids. The alcohol was first treated with NaOCl and TEMPO under phase-transfer conditions, followed by NaClO2 oxidation in one pot. This reaction is applicable to a wide range of alcohols and the mild reaction conditions are compatible with many sensitive functional groups, including electron-rich aromatic rings, acid-labile isopropylidene ketal and glycosidic linkages, and oxidation-prone thioacetal, p-methoxybenzyl, and allyl moieties. Several glycosaminoglycans such as heparin, chondroitin, and hyaluronic acid oligosaccharides have been synthesized in high yields by using this new oxidation protocol.
Huang
Lijun
L
Department of Chemistry, The University of Toledo, 2801 W. Bancroft St. MS 602, Toledo, OH 43606, USA.
Teumelsan
Nardos
N
Huang
Xuefei
X
D000438:Alcohols / Q000737:chemistry*; D000975:Antioxidants / Q000737:chemistry; D001593:Benzyl Compounds / Q000138:chemical synthesis; D002240:Carbohydrate Sequence; D002264:Carboxylic Acids / Q000138:chemical synthesis*; D002384:Catalysis; D003497:Cyclic N-Oxides / Q000737:chemistry; D006025:Glycosaminoglycans / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000737:chemistry; D010084:Oxidation-Reduction; D010472:Perchlorates / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization
D000438:Alcohols; D000975:Antioxidants; D001593:Benzyl Compounds; D002264:Carboxylic Acids; D003497:Cyclic N-Oxides; D006025:Glycosaminoglycans; D009844:Oligosaccharides; D010472:Perchlorates; C003959:TEMPO