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Regioselective double capping of cyclodextrin scaffolds

机译:环糊精支架的区域选择性双重封端

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Four different regioselective double capping reactions were applied either to α- or β-cyclodextrin (CD) scaffolds. The first, which relied on the use of a rigid, bulky dialkylating reagent containing two trityl-like subunits, gave access to an A,B,D,E-tetrafunctionalised β-CD regioisomer in large scale reactions. Two further capping reactions, involving the dianions PhP~(2-) and S~(2-), led to the synthesis of new C _1-symmetrical β-cyclodextrins in which pairs of neighbouring glucose units are linked by very short spacers. The last double capping reaction described allowed the high-yield preparation of unprecedented α- and β-cyclodextrins containing two sulfate handles. Proximal capping turned out to be favoured for each of the above difunctional reagents. The structural characterisation of the capped species was achieved by thorough NMR investigations as well as by single-crystal X-ray diffraction studies.
机译:将四种不同的区域选择性双重封端反应应用于α-或β-环糊精(CD)支架。第一个依靠使用含有两个三苯甲基样亚基的刚性的,笨重的二烷基化试剂,可以在大规模反应中获得A,B,D,E-四官能化的β-CD区域异构体。涉及二价阴离子PhP〜(2-)和S〜(2-)的另外两个加帽反应导致了新的C _1对称β-环糊精的合成,其中相邻的葡萄糖单元对通过非常短的间隔基连接。所描述的最后的双封端反应允许高产率地制备含有两个硫酸盐柄的前所未有的α-和β-环糊精。事实证明,对于每种上述双功能试剂而言,近端封端是有利的。通过彻底的NMR研究以及单晶X射线衍射研究获得了被封端物质的结构表征。

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