(2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(octadecanoylamino)-4-octadecene-1-ol | 168412-00-8

• 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: (2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(octadecanoylamino)-4-octadecene-1-ol
• 英文别名: N-[(E,2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-1-hydroxyoctadec-4-en-2-yl]octadecanamide
• CAS: 168412-00-8
• 化学式: C₄₂H₈₅NO₃Si
• 分子量: 680.227
• InChiKey: KCLIXCFRSOOIDA-PUYNVXOJSA-N

物化性质

• 沸点：
  719.4±60.0 °C(Predicted)
• 密度：
  0.892±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.37
• 重原子数：
  47
• 可旋转键数：
  35
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(octadecanoylamino)-4-octadecene-1-ol 在 吡啶 、 氢氟酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 Pyridin-4-ylmethyl-carbamic acid (E)-(2S,3R)-3-hydroxy-2-octadecanoylamino-octadec-4-enyl ester
  参考文献：
  名称：

  Sphingomyelin analogues as inhibitors of sphingomyelinase

  摘要：

  To search for neutral sphingomyelinase inhibitors we designed and synthesized hydrolytically stable analogues of sphingomyelin. The novel compounds 8 and 9 which were replaced the phosphodiester moiety of sphingomyelin with the carbamate moiety showed inhibitory activity with an IC50 value of muM on neutral sphingomyelinase in rat brain microsomes. Compound 8i showed a selective neutral sphingomyelinase inhibitory activity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00360-3
• 作为产物：
  描述：

  (2S,3R,4E)-2-叠氮-3-(叔丁基二甲基硅烷)-赤-鞘氨醇 在 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 吡啶 、 水 为溶剂， 生成 (2S,3R,4E)-3-(tert-butyldimethylsilyloxy)-2-(octadecanoylamino)-4-octadecene-1-ol
  参考文献：
  名称：

  Synthesis of D-erythro-sphingomyelin and of D-erythro-ceramide-1-phosphoinositol

  摘要：

  3-0-Silyl-protected azidosphingosine 3, readily available from D-erythro-azidosphingosine, is transformed into ceramidyl phosphite derivative 5 which is a versatile building block for the synthesis of ceramide-1-0-phosphate and derivatives. This is exhibited for the synthesis of the title compounds 1 and 2.

  DOI：

  10.1016/s0040-4039(00)91820-3

文献信息

• Design and Synthesis of Sphingomyelin-Cholesterol Conjugates and Their Formation of Ordered Membranes
  作者：Nobuaki Matsumori、Norio Tanada、Kohei Nozu、Hiroki Okazaki、Tohru Oishi、Michio Murata

  DOI：10.1002/chem.201100849

  日期：2011.7.25

  synthesized SM–Chol conjugates with functionally designed linker portions to restrain Chol mobility and examined their formation of ordered membranes by a detergent insolubility assay, fluorescence anisotropy experiments, and fluorescence‐quenching assay. In all of the tests, membranes prepared from the conjugates showed properties of ordered domains comparable to a SM–Chol (1:1) membrane. To gain insight

  脂质筏是漂浮在脂质双层海洋中的富含胆固醇（Chol）的微区。尽管人们认为Chol优先与鞘磷脂（如鞘磷脂（SM））相互作用，而不是与甘油磷脂相互作用，但主要由于脂质分子的高迁移率和分子间相互作用较弱，因此尚未确定特异性相互作用的起源。在这项研究中，我们合成了具有功能设计的连接子部分的SM–Chol共轭物，以抑制Chol的迁移，并通过去污剂不溶性测定，荧光各向异性实验和荧光猝灭测定检查了它们的有序膜的形成。在所有测试中，由结合物制备的膜均显示出与SM–Chol（1：1）膜相当的有序结构域特性。为了深入了解由共轭物组成的双层结构，我们用64个分子的共轭物进行了分子动力学模拟，这表明共轭物通过在连接子部分弯曲而形成稳定的双层结构，并且大多数情况下会重现氢键之间的氢键。 SM和Chol部分。这些结果暗示在SM和Chol之间在有序域中的分子识别本质上是由共轭分子再现的，因此证明这些共轭分子可以潜在地用
• Kratzer, Bernd; Schmidt, Richard R., Liebigs Annalen, 1995, # 6, p. 957 - 964
  作者：Kratzer, Bernd、Schmidt, Richard R.

  DOI：——

  日期：——
• Synthesis of D-erythro-sphingomyelin and of D-erythro-ceramide-1-phosphoinositol
  作者：Bernd Kratzer、Thomas G. Mayer、Richard R. Schmidt

  DOI：10.1016/s0040-4039(00)91820-3

  日期：1993.10

  3-0-Silyl-protected azidosphingosine 3, readily available from D-erythro-azidosphingosine, is transformed into ceramidyl phosphite derivative 5 which is a versatile building block for the synthesis of ceramide-1-0-phosphate and derivatives. This is exhibited for the synthesis of the title compounds 1 and 2.
• Sphingomyelin analogues as inhibitors of sphingomyelinase
  作者：Minoru Taguchi、Kikuo Sugimoto、Ken-ichi Goda、Tomoko Akama、Kyoko Yamamoto、Taizo Suzuki、Yasumitsu Tomishima、Mariko Nishiguchi、Koshi Arai、Kenzo Takahashi、Takeo Kobori

  DOI：10.1016/s0960-894x(03)00360-3

  日期：2003.6

  To search for neutral sphingomyelinase inhibitors we designed and synthesized hydrolytically stable analogues of sphingomyelin. The novel compounds 8 and 9 which were replaced the phosphodiester moiety of sphingomyelin with the carbamate moiety showed inhibitory activity with an IC50 value of muM on neutral sphingomyelinase in rat brain microsomes. Compound 8i showed a selective neutral sphingomyelinase inhibitory activity. (C) 2003 Elsevier Science Ltd. All rights reserved.