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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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