3,3'-O-[1,18-octadecan-(8,11-methylidene)methylene]-2,2'-di-O-[(R)-3,7-dimethyloctyl]-1-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-1'-O-benzyl-sn-diglycerol | 643767-60-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 3,3'-O-[1,18-octadecan-(8,11-methylidene)methylene]-2,2'-di-O-[(R)-3,7-dimethyloctyl]-1-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-1'-O-benzyl-sn-diglycerol
• CAS: 643767-60-6
• 化学式: C₆₆H₁₁₄O₁₅
• 分子量: 1147.62
• InChiKey: OGIDFBYAUZAOLI-FBGXONQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.91
• 重原子数：
  81.0
• 可旋转键数：
  49.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  169.81
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  3,3'-O-[1,18-octadecan-(8,11-methylidene)methylene]-2,2'-di-O-[(R)-3,7-dimethyloctyl]-1-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-1'-O-benzyl-sn-diglycerol 在 10percent Pd/C 氢气 作用下， 以 乙醇 为溶剂， 以95%的产率得到3,3'-O-[1,18-octadecan-(8,11-methylidene)methylene]-2,2'-di-O-[(R)-3,7-dimethyloctyl]-1-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-sn-diglycerol
  参考文献：
  名称：

  Supramolecular Self-Assembling Properties of Membrane-Spanning Archaeal Tetraether Glycolipid Analogues

  摘要：

  The self-assembling properties of a new series of archaeal tetraether glycolipid analogues 1 -6 that are characterized by a bipolar architecture with two similar or different gylycosidic and/or phosphate polar heads and a lipid core possessing a cyclopentane unit and/or branched chains were studied by means of differential scanning calorimetry, optical microscopy, X-ray scattering, freeze-fracture electron microscopy and dynamic light scattering. Unsymmetrical phosphate derivatives 1 and 2 spontaneously formed thermostable multilamellar and unilamellar vesicles in which most of the bipolar lipids adopted a trans-membrane conformation, as revealed by freeze-fracture electron microscopy. Supramolecular aggregates of neutral glycolipids 3-6 were found to depend on both the saccharidic polar heads and the chain composition. The presence of one glycosidic residue with rather marked hydrophilic properties, such as the lactosyl moiety, was required to allow the formation of multilamellar vesicles. Surprisingly, the introduction of a cyclopentane unit in the bridging chain was able to induce an apparent two-by-two membrane association: this unusual behaviour might be the result of unsymmetrical interfacial properties of the lipid layer caused by the presence of the cyclopentane unit.

  DOI：

  10.1002/1521-3765(20020201)8:3<585::aid-chem585>3.0.co;2-5
• 作为产物：
  描述：

  3,3'-O-<1,18-octadecan-(8,11-methylidene)methylene>-bis<2-O-<(R)-3,7-dimethyloctyl>-sn-glycerol> 在 N-碘代丁二酰亚胺 、 三乙基硅基三氟甲磺酸酯 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 3,3'-O-[1,18-octadecan-(8,11-methylidene)methylene]-2,2'-di-O-[(R)-3,7-dimethyloctyl]-1-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-1'-O-benzyl-sn-diglycerol
  参考文献：
  名称：

  Supramolecular Self-Assembling Properties of Membrane-Spanning Archaeal Tetraether Glycolipid Analogues

  摘要：

  The self-assembling properties of a new series of archaeal tetraether glycolipid analogues 1 -6 that are characterized by a bipolar architecture with two similar or different gylycosidic and/or phosphate polar heads and a lipid core possessing a cyclopentane unit and/or branched chains were studied by means of differential scanning calorimetry, optical microscopy, X-ray scattering, freeze-fracture electron microscopy and dynamic light scattering. Unsymmetrical phosphate derivatives 1 and 2 spontaneously formed thermostable multilamellar and unilamellar vesicles in which most of the bipolar lipids adopted a trans-membrane conformation, as revealed by freeze-fracture electron microscopy. Supramolecular aggregates of neutral glycolipids 3-6 were found to depend on both the saccharidic polar heads and the chain composition. The presence of one glycosidic residue with rather marked hydrophilic properties, such as the lactosyl moiety, was required to allow the formation of multilamellar vesicles. Surprisingly, the introduction of a cyclopentane unit in the bridging chain was able to induce an apparent two-by-two membrane association: this unusual behaviour might be the result of unsymmetrical interfacial properties of the lipid layer caused by the presence of the cyclopentane unit.

  DOI：

  10.1002/1521-3765(20020201)8:3<585::aid-chem585>3.0.co;2-5