Synthesis of cyclodextrin-based carbohydrate clusters by photoaddition reactions
Synthesis of cyclodextrin-based carbohydrate clusters by photoaddition reactions
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DOI：
10.1021/jo010705z
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发表时间：
2001-12-14
影响因子：
3.6
通讯作者：
Stoddart, JF
中科院分区：
文献类型：
--
作者：
Fulton, DA;Stoddart, JF
描述了均质环糊精基碳水化合物簇的合成，其环糊精环的（a）主面、（b）副面或（c）主面和副面均被β-D-硫代葡萄糖基或D-硫代乳糖基残基全取代。合成方法中的关键步骤，即将碳水化合物残基附着到环糊精环上，通过将位于碳水化合物残基异头中心的硫醇基团光加成到环糊精上的烯丙基醚官能团上，以中等良好的收率（42-70%）进行。然后轻松去除保护基团，得到游离的簇化合物。对这些化合物进行了广泛的一维和二维核磁共振波谱研究，以确定它们的结构并建立它们的均质性，并且进行了简短的计算机分子建模研究，可以估计簇的尺寸。
The syntheses of homogeneous cyclodextrin-based carbohydrate clusters, persubstituted with beta -D-thioglucosyl or D-thiolactosyl residues on either (a) the primary face, (b) the secondary face, or (c) both the primary and the secondary faces of their cyclodextrin tori, are described. The key step in the synthetic methodology, namely the attachment of the carbohydrate residues to the cyclodextrin torus, proceeds in moderate-good yields (42-70%) by the photoaddition of thiol groups, positioned at the anomeric centers of the carbohydrate residues, to allyl ether functions on the cyclodextrins. Facile removal of protecting groups then affords the free cluster compounds. Extensive 1-D and 2-D NMR spectroscopic investigations were performed on these compounds to determine their structures and establish their homogeneities, and a brief computer molecular modeling study allowed estimates of the dimensions of the clusters to be determined.