3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-deoxy-1-O-hexyl-2-octadecanamido-sn-glycerol | 478550-17-3

• 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: 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-deoxy-1-O-hexyl-2-octadecanamido-sn-glycerol
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[(2R)-3-hexoxy-2-(octadecanoylamino)propoxy]oxan-2-yl]methyl benzoate
• CAS: 478550-17-3
• 化学式: C₆₁H₈₁NO₁₂
• 分子量: 1020.31
• InChiKey: IJFWQCNZCRTLNC-VWPCDBLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.3
• 重原子数：
  74
• 可旋转键数：
  40
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-deoxy-1-O-hexyl-2-octadecanamido-sn-glycerol 在 甲醇 、 sodium methylate 作用下， 反应 18.0h， 以77%的产率得到2-deoxy-3-O-β-D-galactopyranosyl-1-O-hexyl-2-octadecanamido-sn-glycerol
  参考文献：
  名称：

  Self-Organizing Properties of Natural and Related Synthetic Glycolipids

  摘要：

  In this article we report on the syntheses, self-organizing properties, and structures of a variety of cerebrosides and related synthetic glycolipids. The thermotropic and lyotropic liquid crystalline properties of the materials were evaluated in detail. All of the families of materials studied exhibited columnar mesophases. In the dry state the aliphatic chains were found to be located on the exterior of the columns, whereas in the wet state the reverse was the case with the polar headgroups on the exterior. Thus, the aliphatic chains, act almost like hydrocarbon solvents in the dry state.

  DOI：

  10.1021/ja020396+
• 作为产物：
  描述：

  (2S)-3-(hexyloxy)-1,2-propanediol 在 吡啶 、 4-二甲氨基吡啶 、 sodium azide 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 四丁基氟化铵 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 81.5h， 生成 3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2-deoxy-1-O-hexyl-2-octadecanamido-sn-glycerol
  参考文献：
  名称：

  Self-Organizing Properties of Natural and Related Synthetic Glycolipids

  摘要：

  In this article we report on the syntheses, self-organizing properties, and structures of a variety of cerebrosides and related synthetic glycolipids. The thermotropic and lyotropic liquid crystalline properties of the materials were evaluated in detail. All of the families of materials studied exhibited columnar mesophases. In the dry state the aliphatic chains were found to be located on the exterior of the columns, whereas in the wet state the reverse was the case with the polar headgroups on the exterior. Thus, the aliphatic chains, act almost like hydrocarbon solvents in the dry state.

  DOI：

  10.1021/ja020396+

文献信息

• Self-Organizing Properties of Natural and Related Synthetic Glycolipids
  作者：Fabienne Dumoulin、Dominique Lafont、Paul Boullanger、Grahame Mackenzie、Georg H. Mehl、John W. Goodby

  DOI：10.1021/ja020396+

  日期：2002.11.1

  In this article we report on the syntheses, self-organizing properties, and structures of a variety of cerebrosides and related synthetic glycolipids. The thermotropic and lyotropic liquid crystalline properties of the materials were evaluated in detail. All of the families of materials studied exhibited columnar mesophases. In the dry state the aliphatic chains were found to be located on the exterior of the columns, whereas in the wet state the reverse was the case with the polar headgroups on the exterior. Thus, the aliphatic chains, act almost like hydrocarbon solvents in the dry state.