RESUMO
[structure: see text] A highly convergent strategy for the synthesis of C3- or C2-symmetric oligosaccharide macrocycles is reported. Molecular modeling indicates these macrocycles possess sterically congested cavities. Weak host-guest interactions are observed that should be beneficial for applications such as functionalized molecular pores.
Assuntos
Carboidratos/química , Carbono/química , Ciclização , Dimerização , Espectroscopia de Ressonância Magnética , Estrutura Molecular , EstereoisomerismoRESUMO
A convergent strategy for the synthesis of beta-cyclodextrin analogues is reported, utilizing preferential cyclodimerization of an azido-alkyne trisaccharide via Cu(I)-catalyzed [3 + 2] dipolar cycloaddition of the alkyne and azide functional groups. The resultant oligosaccharide macrocycle retains the binding propensity of cyclodextrins, as demonstrated by the similar ANS association constants measured for macrocycle 1 and beta-cyclodextrin. This new synthetic strategy opens up new avenues for modular preparation of functionally diverse cyclodextrin analogues that are otherwise inaccessible.
Assuntos
Alcinos/química , Azidas/química , Ciclodextrinas/síntese química , Trissacarídeos/química , Naftalenossulfonato de Anilina/química , Sequência de Carboidratos , Ciclização , Dimerização , Manosídeos/química , Dados de Sequência Molecular , Espectrometria de FluorescênciaRESUMO
The common and biogenetically important sesquiterpene guaiol yields a deep purple color when treated with electrophilic bromine reagents. This interesting color reaction was observed over fifty years ago, but the chemistry of this process has not been investigated. Herein, we present the chemistry of the guaiol color reaction.