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A facile method for oxidation of primary alcohols to carboxylic acids and its application in glycosaminoglycan syntheses.

ABSTRACT: 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.

SUBMITTER: Huang L

PROVIDER: S-EPMC1986577 | biostudies-literature | 2006 Jul

REPOSITORIES: biostudies-literature

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A facile method for oxidation of primary alcohols to carboxylic acids and its application in glycosaminoglycan syntheses.

Huang Lijun L Teumelsan Nardos N Huang Xuefei X

Chemistry (Weinheim an der Bergstrasse, Germany) 20060701 20

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 ...[more]

PMID: 16637084

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