甲基16-[(三甲基硅烷基)氧基]十六烷酸酯 | 21987-14-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 甲基16-[(三甲基硅烷基)氧基]十六烷酸酯
• 英文名称: methyl 16-trimethylsilyloxyhexadecanoate
• 英文别名: 16-(O-Trimethylsilyloxy)-octadecansaeuremethylester；Methyl 16-hydroxyhexadecanoate, TMSi ether；Methyl 16-hydroxyoctadecanoate, TMSi ether；Methyl 16-[(trimethylsilyl)oxy]hexadecanoate
• CAS: 21987-14-4
• 化学式: C₂₀H₄₂O₃Si
• 分子量: 358.637
• InChiKey: XJKMNMXZRQVIAK-UHFFFAOYSA-N

物化性质

• 保留指数：
  2268;2274

计算性质

• 辛醇/水分配系数(LogP)：
  6.47
• 重原子数：
  24
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  甲基16-[(三甲基硅烷基)氧基]十六烷酸酯 、 β-D-葡萄糖五乙酸酯 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 29.0h， 生成 methyl 16-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-hexadecanoate 、 methyl 16-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)-hexadecanoate
  参考文献：
  名称：

  Synthesis of a glycolipid for studying mechanisms of mitochondrial uncoupling proteins

  摘要：

  Glucose-O-omega-palmitic acid is an amphipathic molecule that is useful as a tool for studying the mechanism of mitochondrial uncoupling proteins. The synthesis of this glycolipid is described herein. The study of the reaction of a series of glycosyl donors with appropriate acceptors derived from 16-hydroxyhexadecanoic acid showed that a glycosyl trichloroacetimidate donor was more efficient than thioglycoside, glycosyl halide and glycosyl acetate donors for synthesis of this glycolipid. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.04.004
• 作为产物：
  描述：

  16-羟基棕榈酸 在 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 甲基16-[(三甲基硅烷基)氧基]十六烷酸酯
  参考文献：
  名称：

  Synthesis of a glycolipid for studying mechanisms of mitochondrial uncoupling proteins

  摘要：

  Glucose-O-omega-palmitic acid is an amphipathic molecule that is useful as a tool for studying the mechanism of mitochondrial uncoupling proteins. The synthesis of this glycolipid is described herein. The study of the reaction of a series of glycosyl donors with appropriate acceptors derived from 16-hydroxyhexadecanoic acid showed that a glycosyl trichloroacetimidate donor was more efficient than thioglycoside, glycosyl halide and glycosyl acetate donors for synthesis of this glycolipid. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.04.004

文献信息

• GULACAR, FAZIL O.;BUCHS, ARMAND;SUSINI, ALBERTO, J. CHROMATOGR., 479,(1989) N, C. 61-72
  作者：GULACAR, FAZIL O.、BUCHS, ARMAND、SUSINI, ALBERTO

  DOI：——

  日期：——
• Synthesis of a glycolipid for studying mechanisms of mitochondrial uncoupling proteins
  作者：Sebastien G. Gouin、Wayne Pilgrim、Richard K. Porter、Paul V. Murphy

  DOI：10.1016/j.carres.2005.04.004

  日期：2005.6

  Glucose-O-omega-palmitic acid is an amphipathic molecule that is useful as a tool for studying the mechanism of mitochondrial uncoupling proteins. The synthesis of this glycolipid is described herein. The study of the reaction of a series of glycosyl donors with appropriate acceptors derived from 16-hydroxyhexadecanoic acid showed that a glycosyl trichloroacetimidate donor was more efficient than thioglycoside, glycosyl halide and glycosyl acetate donors for synthesis of this glycolipid. (c) 2005 Elsevier Ltd. All rights reserved.