2A,6A-F-Hepta-O-tert-butyldimethylsilyl α-cyclodextrin - A carbohydrate undecaol with all OH groups visible in NMR indicative of a partially disrupted hydrogen bond network.
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引用次数: 0
Abstract
During a synthesis of the well-known and useful building block 6A-F-hexa-O-tert-butyldimethylsilyl α-cyclodextrin (2) by silylation of α-cyclodextrin (1) we isolated as a byproduct the oversilylated 2A,6A-F-hepta-O-tert-butyldimethylsilyl α-cyclodextrin (3) where one 2-OH group has also been silylated. This unsymmetrical new compound has a remarkable 1H NMR spectrum in CDCl3 where all 11 alcohol groups are visible. We have analyzed the spectrum of 3 using 1D and 2D 800 MHz NMR and are able to assign all the 11 alcohol protons. The remarkable chemical shifts of these protons are interpreted as being due to a partial disruption of an otherwise efficient hydrogen bond network.
期刊介绍：
Carbohydrate Research publishes reports of original research in the following areas of carbohydrate science: action of enzymes, analytical chemistry, biochemistry (biosynthesis, degradation, structural and functional biochemistry, conformation, molecular recognition, enzyme mechanisms, carbohydrate-processing enzymes, including glycosidases and glycosyltransferases), chemical synthesis, isolation of natural products, physicochemical studies, reactions and their mechanisms, the study of structures and stereochemistry, and technological aspects.
Papers on polysaccharides should have a "molecular" component; that is a paper on new or modified polysaccharides should include structural information and characterization in addition to the usual studies of rheological properties and the like. A paper on a new, naturally occurring polysaccharide should include structural information, defining monosaccharide components and linkage sequence.
Papers devoted wholly or partly to X-ray crystallographic studies, or to computational aspects (molecular mechanics or molecular orbital calculations, simulations via molecular dynamics), will be considered if they meet certain criteria. For computational papers the requirements are that the methods used be specified in sufficient detail to permit replication of the results, and that the conclusions be shown to have relevance to experimental observations - the authors'' own data or data from the literature. Specific directions for the presentation of X-ray data are given below under Results and "discussion".
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