RBM1-33 | 1439377-21-5

• 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: RBM1-33
• 英文别名: N-[(2S,3R)-3-hydroxyoctadecan-2-yl]octanamide
• CAS: 1439377-21-5
• 化学式: C₂₆H₅₃NO₂
• 分子量: 411.712
• InChiKey: IRCLJCDQFWJKJI-LOSJGSFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  29
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4S,5R)-4-methyl-5-pentadecyloxazolidin-2-one 在 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.17h， 生成 RBM1-33
  参考文献：
  名称：

  Straightforward Access to Spisulosine and 4,5-Dehydrospisulosine Stereoisomers: Probes for Profiling Ceramide Synthase Activities in Intact Cells

  摘要：

  A stereoselective synthesis of spisulosine (ES285) and 4,5-dehydrospisulosine stereoisomers is described. Hydrozirconation of 1-pentadecyne with Schwartz reagent, followed by diastereocontrolled addition to L- or D-alaninal afforded the required 2-amino-1,3-diol framework. The resulting sphingoid bases revealed as excellent probes for the profiling of ceramide synthase activity in intact cells. Among the sphingoid bases described in this work, spisulosine (ES285), RBM1-77, and RBM1-73 were the most suitable ones because of their highest acylation rates. These molecules should prove useful to study the role of the different ceramide synthases and the resulting N-acyl (dihydro)ceramides in cell fate.

  DOI：

  10.1021/jo400440z

文献信息

• Straightforward Access to Spisulosine and 4,5-Dehydrospisulosine Stereoisomers: Probes for Profiling Ceramide Synthase Activities in Intact Cells
  作者：José Luis Abad、Ingrid Nieves、Pedro Rayo、Josefina Casas、Gemma Fabriàs、Antonio Delgado

  DOI：10.1021/jo400440z

  日期：2013.6.21

  A stereoselective synthesis of spisulosine (ES285) and 4,5-dehydrospisulosine stereoisomers is described. Hydrozirconation of 1-pentadecyne with Schwartz reagent, followed by diastereocontrolled addition to L- or D-alaninal afforded the required 2-amino-1,3-diol framework. The resulting sphingoid bases revealed as excellent probes for the profiling of ceramide synthase activity in intact cells. Among the sphingoid bases described in this work, spisulosine (ES285), RBM1-77, and RBM1-73 were the most suitable ones because of their highest acylation rates. These molecules should prove useful to study the role of the different ceramide synthases and the resulting N-acyl (dihydro)ceramides in cell fate.