Synthesis and characterisation of some lipophilic per(2,6-di-O-alkyl)cyclomalto-oligosaccharides

Article abstract of DOI:10.1016/0008-6215(91)80033-J

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 deg C.After reaction for 3-9 days, the per(2,6-di-O-alkyl)-CDs were formed.The regiospecifity 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 (37percent and 41percent, respectively).The homogeneity of the pattern of substitution was verified by degradation analysis, f.a.b.-m.s., and n.m.r. spectroscopy.