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A new access to homo- and heterodimers of a-, b-, and g-cyclodextrin by a microwave-promoted Huisgen cycloaddition.

  作者 Cravotto, Giancarlo;Mendicuti, Francisco;Martina, Katia;Tagliapietra, Silvia;Robaldo, Bruna;Barge, Alessandro;  
  选自 期刊  SYNLETT;  卷期  2008年-17;  页码  2642-2646  
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[摘要]A new and efficient synthetic protocol for the prepn. of a-, b- and g-cyclodextrin (CD) homo- and heterodimers is presented. A microwave-promoted Huisgen 1,3-dipolar cycloaddn. will efficiently link together monoazido and monoacetylenic CD derivs. through a 1,2,3-triazole bridge. This well-known click reaction provides a versatile method to yield 'head-to-tail' and 'tail-to-tail' CD dimers in a broad range of combinations. Such an easy access to this kind of mol. architecture may be used to fashion ad hoc tailored CD cavities such as pinching-type structures to be exploited as nano-sized reactors or mol. carriers. Preliminary ests. of the relative distances and orientations of the two CD units in each kind of dimer were obtained by mol. dynamics simulations and related calcns.

 
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