Site-Selective Dehydroxy-Chlorination of Secondary Alcohols in Unprotected Glycosides
作者:Ji Zhang、Niels R. M. Reintjens、Jayaraman Dhineshkumar、Martin D. Witte、Adriaan J. Minnaard
DOI:10.1021/acs.orglett.2c01992
日期:2022.7.29
To circumvent protecting groups, the site-selective modification of unprotected glycosides is intensively studied. We show that site-selective oxidation, followed by treatment of the corresponding trityl hydrazone with tert-butyl hypochlorite and a H atom donor provides an effective way to introduce a chloride substituent in a variety of mono- and disaccharides. The stereoselectivity can be steered
为了规避保护基团,对未受保护的糖苷的位点选择性修饰进行了深入研究。我们表明,位点选择性氧化,然后用次氯酸叔丁酯和 H 原子供体处理相应的三苯甲基腙,提供了一种在各种单糖和二糖中引入氯化物取代基的有效方法。立体选择性是可以控制的,并且还描述了一种新的孪生二氯化反应。这一策略挑战了导致过度氯化的现有方法。