RBM1-75 | 1439377-30-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: RBM1-75
• 英文别名: (2R,3R)-2-aminooctadecan-3-ol
• CAS: 1439377-30-6
• 化学式: C₁₈H₃₉NO
• 分子量: 285.514
• InChiKey: YRYJJIXWWQLGGV-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-十五炔 在 Schwartz's reagent 、 5wt.% Rh on activated alumina 、 水 、 氢气 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 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 21.0h， 生成 RBM1-75
  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

• Highly diastereoselective total synthesis of the anti-tumoral agent (±)-Spisulosine (ES285) from a Morita–Baylis–Hillman adduct
  作者：Giovanni W. Amarante、Mayra Cavallaro、Fernando Coelho

  DOI：10.1016/j.tetlet.2010.02.169

  日期：2010.5

  We disclose herein a new approach for the highly diastereoselective total synthesis of the anti-tumoral agent (±)-Spisulosine. The synthesis was accomplished in seven steps with an overall yield of 10%. The key step involves the transformation of a Morita–Baylis–Hillman into an acyloin, which was subsequently used as substrate in a highly diastereoselective reductive amination reaction.

  我们在此公开了一种用于抗肿瘤剂（±）-螺磺洛辛的高度非对映选择性全合成的新方法。合成以七个步骤完成，总产率为10％。关键步骤涉及将Morita–Baylis–Hillman转化为酰基lo，随后将其用作高度非对映选择性还原胺化反应的底物。
• 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.