Guieu Samuel, Sollogoub Matthieu
UPMC Univ Paris 06, Institut de Chimie Moléculaire (FR 2769), Laboratoire de Chimie Organique (UMR CNRS 7611), 4 place Jussieu, C. 181, F-75005 Paris, France.
J Org Chem. 2008 Apr 4;73(7):2819-28. doi: 10.1021/jo7027085. Epub 2008 Mar 12.
Introduction of one or more functions on a cyclodextrin in a regioselective manner is a complex task. The discovery of a blueprint strategy involving regioselective deprotection reactions of fully protected cyclodextrins, instead of functionalization of native cyclodextrins, allowed us to propose an efficient alternative to reach this goal. In this paper, we have applied previously delineated strategies, based on steric decompression, to duplicate our deprotection reaction, using a combination of mono- or di-deprotections to access cyclodextrins with two, three and five points of attachment for one, two or three different new functions. The patterns of multi-functionalization delineated here are not accessible by any other methods. Indeed, it is the first time ever a cyclodextrin bearing four different groups is synthesized in a completely controlled manner. This work paves the way to the use of cyclodextrins as multi-functional macrocyclic scaffolds, a use they have long been meant for, but lack of reliable functionalization methods hindered this development.
以区域选择性方式在环糊精上引入一种或多种官能团是一项复杂的任务。一种涉及全保护环糊精区域选择性脱保护反应而非天然环糊精官能化的蓝图策略的发现，使我们能够提出实现这一目标的有效替代方法。在本文中，我们应用了先前基于空间减压描述的策略来重复我们的脱保护反应，使用单脱保护或双脱保护的组合来获得具有一个、两个或三个不同新官能团的两个、三个和五个连接点的环糊精。这里描述的多官能化模式是任何其他方法都无法实现的。事实上，这是首次以完全可控的方式合成带有四个不同基团的环糊精。这项工作为将环糊精用作多功能大环支架铺平了道路，长期以来它们一直被用于此用途，但缺乏可靠的官能化方法阻碍了这一发展。
