Abstract
Cyclomalto-hexa-, -hepta-, and -octa-ose (cyclodextrins; α-, β-, and γ-CD) were alkylated severally using propyl, butyl, pentyl, 3-methylbutyl, and dodecyl bromides and NaOH in methyl sulfoxide at 23°. After reaction for 3–9 days, the per(2,6-di- O-alkyl)-CDs were formed. The regiospecificity of these alkylations was higher than for methylations. The best yields of crystalline products were obtained for the butyl derivatives of α- and β-CD (37% and 41%, respectively). The homogeneity of the pattern of substitution was verified by degradation analysis, f.a.b.-m.s., and n.m.r. spectroscopy.
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