Synthesis of two mono-deoxy beta-cyclodextrin derivatives as useful tools for confirming DIBAL-H promoted bis-de-O-methylation mechanism
- Xiao, Su Long
- Zhou, De Min
- Yang, Ming
- Yu, Fei
- Zhang, Li He
- Sinay, Pierre
- Zhang, Yong Min
DOIAbstract
Diisobutylaluminium hydride (DIBAL-H) promotes secondary rim regioselective bis-de-O-methylation of permethylated beta-cyclodextrin (beta-CD) to give diol 2. To gain an insight into the mechanism of this remarkable regioselective behavior, two corresponding permethylated beta-CDs with an alcohol function at either 2- or 3-position were synthesized in our previous study. As a step further to this work, the two compounds were subjected to deoxygenation reaction with tributyltin hydride in the present of 2,2'-azobisisobutyronitrile affording the corresponding 2- and 3-deoxy permethylated beta-CD derivatives (19 and 16). The structures of these two compounds were characterized by 1D and 2D NMR and HRMS. Compounds 16 and 19 were unable to r...
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