Desvergnes Stéphanie, Vallée Yannick, Py Sandrine
Département de Chimie Moléculaire (SERCO), CNRS-Université Joseph Fourier, Grenoble Cedex, France.
Org Lett. 2008 Jul 17;10(14):2967-70. doi: 10.1021/ol8007759. Epub 2008 Jun 21.
A general method to prepare a new class of carbohydrate-derived, enantiomerically pure polyhydroxypyrroline N-oxides from their alkoxy (protected) derivatives is presented. Boron trichloride is shown to cleave efficiently benzyl ethers and ketals without affecting the imine N-oxide functionality of nitrones. The same reagent (BCl3) also allowed the efficient synthesis of a polyhydroxylated N-hydroxypyrrolidine, giving access to a novel class of N-hydroxyiminosugars.
本文介绍了一种从其烷氧基（保护）衍生物制备一类新型碳水化合物衍生的对映体纯多羟基吡咯啉N-氧化物的通用方法。结果表明，三氯化硼能有效裂解苄基醚和缩酮，而不影响硝酮的亚胺N-氧化物官能团。同一试剂（BCl₃）还能高效合成多羟基化的N-羟基吡咯烷，从而获得一类新型的N-羟基亚氨基糖。
