2-hexyldecyl α-D-glucopyranoside | 1352444-35-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-hexyldecyl α-D-glucopyranoside
• 英文别名: (2S,3R,4S,5S,6R)-2-(2-hexyldecoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1352444-35-9
• 化学式: C₂₂H₄₄O₆
• 分子量: 404.588
• InChiKey: ZTENSBWXCKMSHZ-AVGHQTNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 甲醇 、 sodium methylate 作用下， 生成 2-hexyldecyl α-D-glucopyranoside
  参考文献：
  名称：

  A reevaluation of the epimeric and anomeric relationship of glucosides and galactosides in thermotropic liquid crystal self-assemblies

  摘要：

  Anomers and epimers alpha- and beta-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 p-glucosides and the corresponding alpha-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, alpha-gluco/beta-galactoside. A set of alpha-configurated Guerbet glucosides as well as octyl alpha-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. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.10.032

文献信息

• A reevaluation of the epimeric and anomeric relationship of glucosides and galactosides in thermotropic liquid crystal self-assemblies
  作者：Rauzah Hashim、Seyed M. Mirzadeh、Thorsten Heidelberg、Hiroyuki Minamikawa、Tanaka Yoshiaki、Akhiko Sugimura

  DOI：10.1016/j.carres.2011.10.032

  日期：2011.12

  Anomers and epimers alpha- and beta-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 p-glucosides and the corresponding alpha-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, alpha-gluco/beta-galactoside. A set of alpha-configurated Guerbet glucosides as well as octyl alpha-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. (C) 2011 Elsevier Ltd. All rights reserved.