A novel synthesis of ethyl carbonate derivatives of β-cyclodextrin

The carbonate ester derivatives of β-cyclodextrin play a very important role in several fields, such as catalytic reaction and enantiomer separation. In this work, a novel synthesis process of the β-cyclodextrin carbonate ester has been investigated through the reaction between β-cyclodextrin and diethyl carbonate with anhydrous potassium carbonate as catalyst. The compounds were separated by semi-preparative chromatography and characterized by FT-IR, MS, 1H NMR, and 13C NMR spectroscopy. The position of the substituent was confirmed by 13C NMR and this conclusion coincides with the analyses of MS and 1H NMR in the main. The yield of the mono-6-O-ethoxycarbonyl β-CD is 65.8%.

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► A novel method for the synthesis of the ethyl carbonate derivatives of β-CD was studied which used the diethyl carbonate as ethoxycarbonylating reagent in place of the α,ω-diols and the carbonyldiimidazole. The raw material and process are green and environmentally friendly.
► The synthesis of the ethyl carbonate derivatives of β-CD was achieved in one step without protection or deprotection steps. The process is simple and convenient.
► The synthesis of the ethyl carbonate derivatives of β-CD was achieved with good yield.