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

✍ Scribed by Gerhard Wenz

Publisher: Elsevier Science
Year: 1991
Tongue: English
Weight: 770 KB
Volume: 214
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(91)80033-j

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✦ Synopsis

Cyclomalto-hexa-, -hepta-, and -octa-ose (cyclodextrins; a-, /?-, and y-CD) were alkylated severally using propyl, butyl, pentyl, 3-methylbutyl, and dodecyl bromides and NaOH in methyl sulfoxide at 23". After reaction for 339 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 a-arid/3--CD (37% and41 %, 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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