螯合辅助下温和中性条件下吡啶酯的活化合成糖苷氯（溴）化物。
Synthesis of Glycosyl Chlorides and Bromides by Chelation Assisted Activation of Picolinic Esters under Mild Neutral Conditions.
机构信息
School of Pharmacy , University of Wisconsin-Madison , 777 Highland Avenue , Madison , Wisconsin 53705 , United States.
Department of Chemistry , University of Wisconsin-Madison , 1101 University Avenue , Madison , Wisconsin 53706 , United States.
出版信息
Org Lett. 2020 Feb 21;22(4):1495-1498. doi: 10.1021/acs.orglett.0c00078. Epub 2020 Feb 6.
Abstract
A general method has been developed for the formation of glycosyl chlorides and bromides from picolinic esters under mild and neutral conditions. Benchtop stable picolinic esters are activated by a copper(II) halide species to afford the corresponding products in high yields with a traceless leaving group. Rare β glycosyl chlorides are accessible via this route through neighboring group participation. Additionally, glycosyl chlorides with labile protecting groups previously not easily accessible can be prepared.
摘要
已经开发出一种从吡啶酸酯在温和和中性条件下形成糖基氯化物和溴化物的通用方法。通过铜（II）卤化物物种活化台式稳定的吡啶酸酯，以无残留离去基团的方式高产率得到相应产物。通过邻基参与可以通过此途径获得罕见的β糖基氯化物。此外，可以制备以前不容易获得的带有不稳定保护基的糖基氯化物。
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