Fenger Thomas Hauch, Marinescu Lavinia G, Bols Mikael
Department of Chemistry, University of Aarhus, DK-8000, Denmark.
Org Biomol Chem. 2009 Mar 7;7(5):933-43. doi: 10.1039/b814245a. Epub 2009 Jan 21.
A series of alpha-cyclodextrin derivatives containing a 3, 4 or 5 membered ether-linked bridge between the 6A and 6D oxygen atoms, with and without a ketone, were prepared. The synthesis used perbenzylated alpha-cyclodextrin A,D-diol as a starting material upon which O-alkylation and further modifications led to the di-O-(buta-1,4-diyl), the di-O-(penta-1,5-diyl) and the di-O-(buta-2-on-1,4-diyl) derivatives, which were debenzylated, and compared with the previously reported di-O-(propa-2-on-1,3-diyl) derivative. Permethylated derivatives of the di-O-(propa-2-on-1,3-diyl) and the buta-1,4-diyl derivatives were also made. The 6A,6D-di-O-(propa-2-on-1,3-diyl)-6C,6F-di-O-methyl and di-O-pivaloyl derivatives were also prepared. The new compounds were analysed for catalysis of the oxidation of amines and alcohols.
制备了一系列在6A和6D氧原子之间含有3、4或5元醚键桥的α-环糊精衍生物，有酮基和无酮基的都有。合成过程以全苄基化的α-环糊精A，D-二醇为起始原料，通过O-烷基化和进一步修饰得到二-O-(丁-1,4-二基)、二-O-(戊-1,5-二基)和二-O-(丁-2-酮-1,4-二基)衍生物，这些衍生物进行了脱苄基反应，并与先前报道的二-O-(丙-2-酮-1,3-二基)衍生物进行比较。还制备了二-O-(丙-2-酮-1,3-二基)和丁-1,4-二基衍生物的全甲基化衍生物。还制备了6A，6D-二-O-(丙-2-酮-1,3-二基)-6C，6F-二-O-甲基和二-O-新戊酰基衍生物。对新化合物进行了催化胺和醇氧化反应的分析。
