Huang Lijun, Teumelsan Nardos, Huang Xuefei
Department of Chemistry, The University of Toledo, 2801 W. Bancroft St. MS 602, Toledo, OH 43606, USA.
Chemistry. 2006 Jul 5;12(20):5246-52. doi: 10.1002/chem.200600290.
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.
开发了一种便捷的两步一锅法，用于将伯醇转化为羧酸。首先在相转移条件下用次氯酸钠（NaOCl）和2,2,6,6-四甲基哌啶-1-氧化物（TEMPO）处理醇，然后在同一反应容器中进行亚氯酸钠（NaClO₂）氧化。该反应适用于多种醇，温和的反应条件与许多敏感官能团兼容，包括富电子芳环、对酸不稳定的异亚丙基缩酮和糖苷键，以及易氧化的硫代乙缩醛、对甲氧基苄基和烯丙基部分。通过使用这种新的氧化方法，已高产率地合成了几种糖胺聚糖，如肝素、软骨素和透明质酸寡糖。
