3,3'-O-<1,18-octadecan-(8,11-methylidene)methylene>-bis<2-O-<(R)-3,7-dimethyloctyl>-sn-glycerol> | 222984-27-2

• 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>-bis<2-O-<(R)-3,7-dimethyloctyl>-sn-glycerol>
• 英文别名: (2R)-2-[(3R)-3,7-dimethyloctoxy]-3-[7-[3-[7-[(2R)-2-[(3R)-3,7-dimethyloctoxy]-3-hydroxypropoxy]heptyl]cyclopentyl]heptoxy]propan-1-ol
• CAS: 222984-27-2
• 化学式: C₄₅H₉₀O₆
• 分子量: 727.206
• InChiKey: JNNYCFPPYUUQPE-AGLKPHBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.3
• 重原子数：
  51
• 可旋转键数：
  38
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  3-O-trityl-2-O-(R)-3,7-dimethyloctyl-1-O-benzyl-sn-glycerol 在 palladium on activated charcoal 甲酸 、 氢气 、 potassium hydride 作用下， 以 四氢呋喃 、 乙醚 、 乙酸乙酯 为溶剂， 反应 6.33h， 生成 3,3'-O-<1,18-octadecan-(8,11-methylidene)methylene>-bis<2-O-<(R)-3,7-dimethyloctyl>-sn-glycerol>
  参考文献：
  名称：

  新型古生四醚糖脂类似物的合成方法。

  摘要：

  已经制备了对称和不对称的古细菌四醚糖脂类似物。合成是基于从多种手性起始原料精制脂质核心，然后同时或相继引入极性头基。阐述了合成立体化学定义的脂质14-16的三个途径（AC），这些脂质的特征是直连接间隔基和两个分别在sn-3和sn-2位置与甘油单元相连的二氢香茅烷基链。途径C似乎对于合成四醚9特别有利，该四醚9具有在嗜热嗜酸脂质中发现的环戊烷单元。通过二醇14-16与β-D-半乳糖呋喃糖基供体31的反应，以49-53％的产率生产了二糖基化脂质4-6。

  DOI：

  10.1021/jo9822028

文献信息

• Synthesis and Supramolecular Assemblies of Bipolar Archaeal Glycolipid Analogues Containing a <i>cis</i>-1,3-Disubstituted Cyclopentane Ring
  作者：Mickaëlle Brard、Walter Richter、Thierry Benvegnu、Daniel Plusquellec

  DOI：10.1021/ja049805n

  日期：2004.8.1

  and cryotransmission electron microscopy experiments clearly demonstrated unprecedented glycolipid supramolecular organizations involving two-by-two monolayer associations coupled with interconnection and fusion phenomena. Furthermore, a significant difference in the hydration properties and in the lyotropic liquid crystalline behavior of bipolar lipids 1-2 was found depending on the position of the

  不对称古菌四醚糖脂类似物 1-2 纳入 1,3-二取代环戊烷环进入桥链已被合成。环戊烷以完全受控的顺式构型引入脂族链的中间或甘油单元的三个亚甲基与较大的二糖残基相连。冷冻断裂和低温透射电子显微镜实验清楚地证明了前所未有的糖脂超分子组织，涉及两两单层结合以及互连和融合现象。此外，根据环戊烷残基的位置，发现双极脂质 1-2 的水合特性和溶致液晶行为存在显着差异。
• Synthetic Approaches to Novel Archaeal Tetraether Glycolipid Analogues
  作者：Grégory Lecollinet、Rachel Auzély-Velty、Mathieu Danel、Thierry Benvegnu、Grahame Mackenzie、John W. Goodby、Daniel Plusquellec

  DOI：10.1021/jo9822028

  日期：1999.4.1

  Symmetrical and unsymmetrical archaeal tetraether glycolipid analogues have been prepared. The syntheses are based upon the elaboration of lipid cores from versatile chiral starting materials followed by simultaneous or sequential introduction of polar headgroups. Three pathways (A-C) were elaborated for the synthesis of stereochemically defined lipids 14-16 characterized by a straight bridging spacer

  已经制备了对称和不对称的古细菌四醚糖脂类似物。合成是基于从多种手性起始原料精制脂质核心，然后同时或相继引入极性头基。阐述了合成立体化学定义的脂质14-16的三个途径（AC），这些脂质的特征是直连接间隔基和两个分别在sn-3和sn-2位置与甘油单元相连的二氢香茅烷基链。途径C似乎对于合成四醚9特别有利，该四醚9具有在嗜热嗜酸脂质中发现的环戊烷单元。通过二醇14-16与β-D-半乳糖呋喃糖基供体31的反应，以49-53％的产率生产了二糖基化脂质4-6。
• Supramolecular Self-Assembling Properties of Membrane-Spanning Archaeal Tetraether Glycolipid Analogues
  作者：Grégory Lecollinet、Annette Gulik、Grahame Mackenzie、John W. Goodby、Thierry Benvegnu、Daniel Plusquellec

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

  日期：2002.2.1

  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.