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

Chemistry : a European Journal
Lijun HuangXuefei Huang

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.

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Citations

Jul 31, 2007·Glycoconjugate Journal·Chinmoy Mukherjee, Anup Kumar Misra
Sep 22, 2009·The Journal of Organic Chemistry·Xiaowei LuXuefei Huang
Nov 18, 2015·The Journal of Organic Chemistry·Steven B DulaneyXuefei Huang
Nov 18, 2015·Carbohydrate Polymers·Tomáš BobulaVladimír Velebný
Jul 14, 2016·Chemical Reviews·Marco MendeStefan Bräse
Oct 19, 2016·Organic & Biomolecular Chemistry·Gydo van der HeijdenRomano V A Orru
Oct 14, 2006·Chemistry : a European Journal·Lijun Huang, Xuefei Huang
Oct 7, 2011·Beilstein Journal of Organic Chemistry·Abhishek Santra, Anup Kumar Misra
Mar 16, 2019·Beilstein Journal of Organic Chemistry·Arin GucchaitAnup Kumar Misra
Dec 21, 2010·Chemical Communications : Chem Comm·Pawel CzechuraNiels-Christian Reichardt
Jul 26, 2011·Chemistry : a European Journal·Gopinath TiruchinapallyXuefei Huang
Mar 19, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Andrea TemperiniCarlo Siciliano
May 23, 2014·Organic & Biomolecular Chemistry·Kiran Chinthapally, Sundarababu Baskaran
Sep 5, 2008·Chemistry : a European Journal·Jasper DinkelaarGijsbert A van der Marel
Aug 5, 2008·The Journal of Organic Chemistry·Vishal Kumar Rajput, Balaram Mukhopadhyay
Aug 30, 2017·Organic Letters·Sherif RamadanXuefei Huang
Dec 1, 2017·Organic Letters·G Sudhakar ReddyDebendra K Mohapatra

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