octadecyl 2-deoxy-α-D-arabino-hexopyranoside | 1194219-22-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: octadecyl 2-deoxy-α-D-arabino-hexopyranoside
• 英文别名: C18-2d-α-Glc；(2R,3S,4R,6S)-2-(hydroxymethyl)-6-octadecoxyoxane-3,4-diol
• CAS: 1194219-22-1
• 化学式: C₂₄H₄₈O₅
• 分子量: 416.642
• InChiKey: UJWMIQSUSRHYHQ-LWSSLDFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  29
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 甲醇 、 sodium methylate 作用下， 反应 8.0h， 生成 octadecyl 2-deoxy-α-D-arabino-hexopyranoside 、 octadecyl 2-deoxy-β-D-arabino-hexopyranoside
  参考文献：
  名称：

  Effect of the C-2 hydroxyl group on the mesomorphism of alkyl glycosides: synthesis and thermotropic behavior of alkyl 2-deoxy-d-arabino-hexopyranosides

  摘要：

  A homologous series of alkyl 2-deoxy-alpha-D-arabino-hexopyranosides and alkyl 2-deoxy-beta-D-arabino-hexopyranosides were synthesized, upon glycosylation of 1-alkanols (from C-8 to C-18 alkanols) with ethyl 2-deoxy-3,4,6-tri-O-acetyl-1-thio-D-arabino-hexopyranoside, followed by a deprotection. The thermotropic behavior of these new types of alkyl glycosides was investigated. It was observed that the beta-anomers of these alkyl glycosides, bearing nonyl to tetradecyl alkyl chain are mesomorphic, exhibiting monotropic smectic A phase. In contrast, the alpha-anomers are all non-mesomorphic. An effort to identify the liquid crystalline behavior of binary mixtures of the alpha- and beta-anomers was undertaken and it was found that mixtures containing equimolar amounts of the anomers exhibited rnesomorphic behavior. A fine balance of the hydrophilic and hydrophobic components within the molecule is also found to be important for the alkyl 2-deoxy glycosides to form the mesophase. (C) 2008 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2008.07.008