3-O-[4'-O-(2'',3'',4'',6''-tetra-O-acetyl-α-D-glucopyranosyl)-2',3',6'-tri-O-acetyl-β-D-glucopyranosyl]-sn-glycerol | 429677-90-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-[4'-O-(2'',3'',4'',6''-tetra-O-acetyl-α-D-glucopyranosyl)-2',3',6'-tri-O-acetyl-β-D-glucopyranosyl]-sn-glycerol
• CAS: 429677-90-7
• 化学式: C₂₉H₄₂O₂₀
• 分子量: 710.64
• InChiKey: GNWCVZUHPMESHJ-RTYUQHJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.02
• 重原子数：
  49.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  261.48
• 氢给体数：
  2.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  3-O-[4'-O-(2'',3'',4'',6''-tetra-O-acetyl-α-D-glucopyranosyl)-2',3',6'-tri-O-acetyl-β-D-glucopyranosyl]-sn-glycerol 在 甲醇 、 sodium methylate 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 生成 (2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Synthesis and mesogenic properties of glycosyl diacylglycerols

  摘要：

  We synthesised glycosyl diacylglycerols bearing unsaturated or chiral methyl branched fatty acid chains. The thermotropism was measured with polarising microscopy and additionally the lyotropism with the contact preparation method. The synthesised compounds displayed thermotropic S-A (lamellar), cubic and columnar phases and investigation of the lyotropic phase behaviour led to the observation of inverted bicontinuous cubic V-H phases, lamellar L-x phases and normal bicontinuous cubic V-I phases, The phases are discussed with respect to the chemical structures that have been varied systematically to derive structure-property relationships. (C) 2002 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(01)00202-x
• 作为产物：
  描述：

  1,2-di-O-benzyl-3-O-[4'-O-(2'',3'',4'',6''-tetra-O-acetyl-α-D-glucopyranosyl)-2',3',6'-tri-O-acetyl-β-D-glucopyranosyl]-sn-glycerol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 溶剂黄146 、 乙酸乙酯 为溶剂， 以92%的产率得到3-O-[4'-O-(2'',3'',4'',6''-tetra-O-acetyl-α-D-glucopyranosyl)-2',3',6'-tri-O-acetyl-β-D-glucopyranosyl]-sn-glycerol
  参考文献：
  名称：

  Synthesis and mesogenic properties of glycosyl diacylglycerols

  摘要：

  We synthesised glycosyl diacylglycerols bearing unsaturated or chiral methyl branched fatty acid chains. The thermotropism was measured with polarising microscopy and additionally the lyotropism with the contact preparation method. The synthesised compounds displayed thermotropic S-A (lamellar), cubic and columnar phases and investigation of the lyotropic phase behaviour led to the observation of inverted bicontinuous cubic V-H phases, lamellar L-x phases and normal bicontinuous cubic V-I phases, The phases are discussed with respect to the chemical structures that have been varied systematically to derive structure-property relationships. (C) 2002 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(01)00202-x

文献信息

• Synthesis and mesomorphic properties of glycosyl dialkyl- and diacyl-glycerols bearing saturated, unsaturated and methyl branched fatty acid and fatty alcohol chains
  作者：Götz Milkereit、Sven Gerber、Klaus Brandenburg、Michael Morr、Volkmar Vill

  DOI：10.1016/j.chemphyslip.2005.01.004

  日期：2005.5

  Glycosyl dialkyl- and diacyl-glycerols bearing saturated, unsaturated or chiral methyl branched chains in the tail and disaccharide and trisaccharide carbohydrate headgroups were synthesised. Standard procedures were used for the preparation of the educts and the glyco lipids: trichloracetimidate procedure for the preparation of long-chained compounds, glycosylation using the beta-peracetate and boron

  合成了在尾部带有饱和，不饱和或手性甲基支链的糖基二烷基和二酰基甘油，以及二糖和三糖碳水化合物头基。使用标准程序制备离析物和糖脂：使用三氯乙亚胺酸酯程序制备长链化合物，使用β-过乙酸酯和三氟化硼醚化物进行糖基化成功制备了中等烷基链长的脂质。根据公开的方法，通过多步合成提供了酯的制备。因此，在几个合成步骤中以高收率合成了几种脂质。不饱和或甲基支链的引入导致环境温度下的液晶性，因为这些化合物将用作生物系统的模型化合物。这些化合物的生物物理特性将在随后的论文中报道。