- A reevaluation of the epimeric and anomeric relationship of glucosides and galactosides in thermotropic liquid crystal self-assemblies
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Anomers and epimers α- and β-gluco and -galactosides are expected to behave differently. However, recent results on a series of Guerbet glycosides have indicated similar liquid crystal clearing temperatures for pure β-glucosides and the corresponding α-galactosides. This observation has led to speculation on similarities in the self-assembly interactions between the two systems, attributed to the trans-configuration of the 4-OH group and the hydrophobic aglycon. Previous simulations on related bilayers systems support this hypothesis, by relating this clearing transition temperature to intralayer (sugar-sugar) hydrogen bonding. In order to confirm the hypothesis, the comparison was expanded to include the cis-configurated pair, that is, α-gluco/β-galactoside. A set of α-configurated Guerbet glucosides as well as octyl α-galactoside were prepared and their thermotropic phase behavior studied. The data obtained enabled a complete comparison of the isomers of interest. While the results in general are in line with a pairing of the stereo-isomers according to the indicated cis/trans-configuration, differences within the pairs can be explained based on the direction of hydrogen bonds from a simple modeling study.
- Hashim, Rauzah,Mirzadeh, Seyed M.,Heidelberg, Thorsten,Minamikawa, Hiroyuki,Yoshiaki, Tanaka,Sugimura, Akhiko
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experimental part
p. 2948 - 2956
(2012/01/04)
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- Synthesis of C7-C16-alkyl glycosides: Part III - Synthesis of alkyl D-galactopyranosides in the presence of tin(IV) chloride as a Lewis acid catalyst
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The Lewis acid catalyzed glycosylation reaction of β-peracetylated sugar derivative (galactose) with fatty alkanols is used in a synthesis of C7-C16-alkyl galactopyranosides. The process occurs under the influence of tin(IV) chloride as a Lewis acid catalyst.
- Konstantinovi?,Dimitrijevi?,Radulovi?
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p. 598 - 603
(2007/10/03)
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- Synthesis of C7-C16-alkyl glycosides: Part I - Synthesis of alkyl D-glucopyranosides in the presence of tin (IV) chloride as a Lewis acid catalyst
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The Lewis acid catalyzed glycosylation reaction of β-peracetylated sugar derivative (glucose) with fatty alkanols is used in a synthesis of C7-C16-alkyl glucopyranosides. The process occurs under the influence of tin (IV) chloride.
- Konstantinovic,Predojevic,Mojsilovic,Dimitrijevic,Milosevic
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p. 796 - 801
(2007/10/03)
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