Communication: A Convenient Synthesis of Per-O-Methylated 6-O-Monosubstituted ß-Cyclodextrins
作者:
Niculina Lupescu,
Catherine K. Y. Ho,
Guochen Jia,
Jiri J. Krepinsky,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1999)
卷期:
Volume 18,
issue 1
页码: 99-104
ISSN:0732-8303
年代: 1999
DOI:10.1080/07328309908543982
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
Cyclodextrins are cyclic oligosaccharides that function as chiral host molecules exhibiting enantioselectivity in reactions with racemic guests1and thus they represent a significant moiety of artificial enzymes.2The most easily obtainable and relatively inexpensive are ß-cyclodextrins (ß-CD), cyclic heptaglucosides in which glucopyranosyl residues are linked by an α(1-4) glycosidic bonds. ß-CD is surprisingly poorly soluble in water (1.8 g in 100 mL)3but the solubility of its derivatives is often significantly better. For instance, ß-CD with all secondary hydroxyls methylated, forms 50% aqueous solutions at room temperature,4and even completely methylated ß-CD is ten times more soluble in water (17 g in 100 mL)5than ß-CD itself. Methylation also alters the binding of the substrates to ß-CD often increasing its specificity and strength,6and renders the hydroxyl groups unreactive. Therefore, it is of interest to prepare derivatives of ß-CD in which the enzyme-mimicking group is bound to one hydroxyl (possibly through a tether) while the rest of the ß-CD moiety is permethylated.
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