stearyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 103328-76-3

• 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: stearyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: octadecyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside；octadecyl-(tetra-O-acetyl-β-D-glucopyranoside)；Octadecyl-(tetra-O-acetyl-β-D-glucopyranosid)；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-octadecoxyoxan-2-yl]methyl acetate
• CAS: 103328-76-3
• 化学式: C₃₂H₅₆O₁₀
• 分子量: 600.791
• InChiKey: QDUHSWMXLTZYND-HXBJCGEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  42
• 可旋转键数：
  27
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  stearyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以92%的产率得到stearyl-β-D-glucopyranoside
  参考文献：
  名称：

  氟化单尾吡喃吡喃糖苷表面活性剂的合成和生物相容性评估

  摘要：

  部分氟化的非离子 表面活性剂 对于一系列生物医学应用（例如肺部给药）感兴趣 毒品使用反向在全氟化碳中的水微乳液。我们在此报告了一系列部分氟化的β- D-吡喃葡萄糖苷的合成与表征表面活性剂 从各自 酒类和BF 3 ·Et 2 O作为过乙酰化的β- D-吡喃葡萄糖苷催化剂。这表面活性剂 氟化物的填充参数 表面活性剂 范围从0.472至0.534（MOPAC计算）或0.562至0.585（根据文献值计算），与 表面活性剂具有类似的部分氟化尾巴。根据初步的生物相容性评估，β- D-吡喃葡萄糖苷表面活性剂在B16F10小鼠黑素瘤细胞系中具有低毒性，并且对兔红细胞的溶血活性相对较低。氟化的表面活性剂 与它们的细胞相比，似乎对培养的细胞毒性较小，并且具有较低的溶血活性 烃类似物。此外，氟化作用似乎同时降低了细胞毒性和溶血活性。已报道其他部分氟化物具有相似的结构-活性关系表面活性剂。总体而言，这些发现表明，表面活性剂

  DOI：

  10.1039/b805015e
• 作为产物：
  描述：

  1,2,3,4,6-alpha-D-葡萄糖五乙酸酯 、 硬脂醇 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 stearyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Thermotropic and lyotropic properties of long chain alkyl glycopyranosides. Part II. Disaccharide headgroups

  摘要：

  We have investigated the thermotropic and lyotropic properties of some long chain alkyl glycosides with disaccharide headgroups. The thermotropism was measured with polarising microscopy and additionally the lyotropism with the contact preparation method, Fourier-transform Infrared (FTIR) spectroscopy, X-ray diffraction and small angle neutron scattering. A broad thermotropic as well as lyotropic polymorphism was found. The compounds displayed thermotropic S-A (lamellar) and cubic phases, and the investigation of the lyotropic phase behaviour led to the observation of inverted bicontinuous cubic V-II phases, lamellar L-alpha phases, normal bicontinuous cubic V-I phases, normal columnar H-I phases, normal discontinuous cubic I-I f phases and lyotropic cholesteric phases. The phases are discussed with respect to the chemical structures that have been varied systematically to derive structure-property relationships. (C) 2000 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(00)00151-1

文献信息

• Hori; Ikegami, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1959, vol. 79, p. 80,82
  作者：Hori、Ikegami

  DOI：——

  日期：——
• Thermotropic and lyotropic properties of long chain alkyl glycopyranosides
  作者：V. Vill、H.M. von Minden、M.H.J. Koch、U. Seydel、K. Brandenburg

  DOI：10.1016/s0009-3084(99)00119-x

  日期：2000.1

  A systematic structure variation of a classical amphiphile (dodecyl-P-D-glucopyranoside) is performed, demonstrating the influence of anomeric linkage, configuration, ring size and flexibility as well as electric charges on the mesophase behaviour. In addition, we have investigated the thermotropic and lyotropic properties of some long chain alkyl glycosides with monosaccharide headgroups. The thermotropism was measured with polarizing microscopy and differential scanning calorimetry, and additionally the lyotropism with FTIR spectroscopy and X-ray diffraction. (C) 2000 Elsevier Science Ireland Ltd. All rights reserved.