Crich David, Li Ming
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
Org Lett. 2007 Oct 11;9(21):4115-8. doi: 10.1021/ol701466u. Epub 2007 Sep 22.
The unexpectedly high reactivity of a (2-benzoxazolyl) per-O-benzoyl-beta-D-thioglucoside and related donors in reactions promoted by copper(II) trifluoromethanesulfonate is revealed, by comparison with the unreactive alpha-anomer, to be the result of neighboring group participation. Revision of the armed-disarmed concept for glycosyl donors is not required.
通过与无反应性的α-异头物比较发现,(2-苯并恶唑基)全-O-苯甲酰基-β-D-硫代葡萄糖苷及相关供体在三氟甲磺酸铜(II)促进的反应中具有出乎意料的高反应性,这是邻基参与的结果。无需修订糖基供体的武装-解除武装概念。