Abstract
This communication reports a novel synthesis route for the preparation of monofunctionalized β-cyclodextrin in a single stage. The approach involves only the in-situ protection of secondary hydroxyl groups as an excellent alternative to the classical procedure involving a series of five steps of protection and deprotection of hydroxyl groups (both primary and secondary ones) belonging to β-cyclodextrin.
Highlights
Introduction and Current Status of theSubjectCyclodextrin (CD) research has increased exponentially during the last fifty years
Due to this wide variety of derivatives, one can wonder how these functional groups affect the general properties of Current Status of theSubjectCyclodextrin (CD) and what specific site should be changed for a particular application; for example, whether an increased water solubility or greater stability of the guest in the CD cavity is desired
These results reveal that by blocking the primary hydroxyl side of β-cyclodextrin (β-CD), there is the benefit of increased water solubility, that all methylated derivatives display, but the maximum binding constant for the inclusion complexes in this series of methylated β-CDs can be obtained
Summary
Introduction and Current Status of theSubjectCyclodextrin (CD) research has increased exponentially during the last fifty years. These results reveal that by blocking the primary hydroxyl side of β-cyclodextrin (β-CD), there is the benefit of increased water solubility, that all methylated derivatives display, but the maximum binding constant for the inclusion complexes in this series of methylated β-CDs can be obtained. A complete change of all 21 hydroxy groups is relatively easy to perform in one step and the yield is quantitative, as demonstrated for per-O-methylated cyclodextrins using Haworth [2] and Irvine–Purdie methylation [3,4] or per-O-(2-hydroxypropyl) cyclodextrins [5], selective primary side derivatization is still in the early development stages, with one notable exception being the modified Appel reaction [6].
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