1,20-bis(α-D-galactopyranosyloxy)eicosane

• 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: 1,20-bis(α-D-galactopyranosyloxy)eicosane
• 英文别名: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[20-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyicosoxy]oxane-3,4,5-triol
• 化学式: C₃₂H₆₂O₁₂
• 分子量: 638.837
• InChiKey: DQLGAYKLHRLIGG-ZWUHGNBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  44
• 可旋转键数：
  25
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  199
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 Rh/Al₂O₃ 、 Grubbs catalyst first generation 氢气 、 sodium methylate 、 zinc(II) chloride 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 26.26h， 生成 1,20-bis(α-D-galactopyranosyloxy)eicosane
  参考文献：
  名称：

  Synthesis and properties of new bolaform and macrocyclic galactose-based surfactants obtained by olefin metathesis

  摘要：

  A series of galactose-based surfactants with various structures likely to display new interesting properties were synthesized. Four monocatenary surfactants were elaborated by microwave-assisted galactosylation of undecanol or 10-undecenol. These compounds were slightly soluble in water. Their tensioactive properties were determined at 45 degreesC. Olefin metathesis was used to synthesize the two single-chain bolaforms from undec-10-enyl galactopyranosides; two pseudomacrocyclic bolaforms were prepared by grafting two carbamates at O-4 and O-4' sugar positions of the single-chain bolaforms. These four surfactants are insoluble in water and undergo monolayer compression. Cyclization of these bolaforms by olefin metathesis led to macrocyclic surfactant analogues of archaeobacterial membrane components. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2004.03.003

文献信息

• Synthesis and properties of new bolaform and macrocyclic galactose-based surfactants obtained by olefin metathesis
  作者：Céline Satgé、Robert Granet、Bernard Verneuil、Yves Champavier、Pierre Krausz

  DOI：10.1016/j.carres.2004.03.003

  日期：2004.5

  A series of galactose-based surfactants with various structures likely to display new interesting properties were synthesized. Four monocatenary surfactants were elaborated by microwave-assisted galactosylation of undecanol or 10-undecenol. These compounds were slightly soluble in water. Their tensioactive properties were determined at 45 degreesC. Olefin metathesis was used to synthesize the two single-chain bolaforms from undec-10-enyl galactopyranosides; two pseudomacrocyclic bolaforms were prepared by grafting two carbamates at O-4 and O-4' sugar positions of the single-chain bolaforms. These four surfactants are insoluble in water and undergo monolayer compression. Cyclization of these bolaforms by olefin metathesis led to macrocyclic surfactant analogues of archaeobacterial membrane components. (C) 2004 Published by Elsevier Ltd.