(4R,5S)-4-methyl-5-pentadecyl-1,3-oxazolidin-2-one | 1439377-28-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R,5S)-4-methyl-5-pentadecyl-1,3-oxazolidin-2-one
• CAS: 1439377-28-2
• 化学式: C₁₉H₃₇NO₂
• 分子量: 311.508
• InChiKey: YGFQERDVWZDGKR-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R,5S)-4-methyl-5-pentadecyl-1,3-oxazolidin-2-one 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以93%的产率得到RBM1-76
  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
• 作为产物：
  描述：

  1-十五炔 在 Schwartz's reagent 、 5wt.% Rh on activated alumina 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， -40.0~20.0 ℃ 、101.33 kPa 条件下， 反应 19.0h， 生成 (4R,5S)-4-methyl-5-pentadecyl-1,3-oxazolidin-2-one
  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.