Capping α‐Cyclodextrin with Cyclotriveratrylene by Triple Disulfide‐Bridge Formation
Capping α‐Cyclodextrin with Cyclotriveratrylene by Triple Disulfide‐Bridge Formation
复制标题
通过三重二硫桥形成用环三藜三烯封端 α-环糊精
DOI：
10.1002/ejoc.201201729
复制
发表时间：
2013
影响因子：
2.8
通讯作者：
J. Chambron
中科院分区：
文献类型：
--
作者：
Frédérique Brégier;J. Lavalle;J. Chambron
二硫键的形成是一个快速的偶联反应，使大环对称受体。本文将其用于制备基于α-环糊精（α-CDX）和环三藜芦烯（CTV）类似物的不对称空腔。因此，通过碘氧化外消旋环三噻吩（3）和全甲基化α-环糊精（PM α-CDX）4的C3-对称三硫醇衍生物的1：1混合物，以11%的分离产率获得非对映体半隐吩2a和2b。值得注意的是，以5：3的非对映体比例获得目标半隐烷。该反应主要产生（34%）单二硫键桥连的PM α-CDX二聚体7，但未检测到三硫键桥连的头对头PM α-CDX二聚体。此外，还观察到已知S-隐精-0.0.0的形成。
Disulfide-bond formation is an expeditious coupling reaction to make macropolycyclic symmetrical receptors. It is used here for the preparation of unsymmetrical cavitands based on α-cyclodextrin (α-CDX) and cyclotriveratrylene (CTV) analogues. Accordingly, diastereomeric hemicryptophanes 2a and 2b were obtained in 11 % isolated yield by the iodine oxidation of a 1:1 mixture of racemic cyclotrithiophenolene (3) and the C3-symmetric trithiol derivative of permethylated α-cyclodextrin (PM α-CDX) 4. Remarkably, the target hemicryptophanes were obtained in a 5:3 diastereomeric ratio. The reaction produced mainly (34 %) a singly disulfide-bridged PM α-CDX dimer 7, however no traces of triply disulfide-bridged head-to-head PM α-CDX dimer were detected. In addition, the formation of the known S-cryptophane-0.0.0 was observed.
影响因子：
3.6
作者：
Au-Yeung, Ho Yu;Pantos, G. Dan;Sanders, Jeremy K. M.
通讯作者：
Sanders, Jeremy K. M.