Selective Silylation of ß-Cyclodextrin

Sonication was used to silylate the seven primary alcohols of ß-cyclodextrin. The sonication reaction produced yields comparable to published procedures and reduced the time of silylation by 75% (1).
The reaction of ß-cyclodextrin and tert-Butyldimethylsilyl chloride in dry pyridine resulted in a 71% yield of Heptakis(6-O-tert-Butyldimethylsilyl)- ß-cyclodextrin.¹ H NMR and ¹³C NMR were used to characterize the product.
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Abstract/Description: Sonication was used to silylate the seven primary alcohols of ß-cyclodextrin. The sonication reaction produced yields comparable to published procedures and reduced the time of silylation by 75% (1). The reaction of ß-cyclodextrin and tert-Butyldimethylsilyl chloride in dry pyridine resulted in a 71% yield of Heptakis(6-O-tert-Butyldimethylsilyl)- ß-cyclodextrin.¹ H NMR and ¹³C NMR were used to characterize the product.
Subject(s): Undergraduate Research
Date Issued: 2021