(2S,3S)-3-azido-2-((methylsulfonyl)oxy)-3-phenylpropyl pivalate | 1026155-30-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S)-3-azido-2-((methylsulfonyl)oxy)-3-phenylpropyl pivalate
• 英文别名: [(2S,3S)-3-azido-2-methylsulfonyloxy-3-phenylpropyl] 2,2-dimethylpropanoate
• CAS: 1026155-30-5
• 化学式: C₁₅H₂₁N₃O₅S
• 分子量: 355.415
• InChiKey: JOZOQCRHFAQGNV-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-azido-2-((methylsulfonyl)oxy)-3-phenylpropyl pivalate 在 caesium carbonate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以23%的产率得到(2R)-2-[(S)-azido(phenyl)methyl]oxirane
  参考文献：
  名称：

  Discovery of Orally Active Hydroxyethylamine Based SPPL2a Inhibitors

  摘要：

  SPPL2a (Signal Peptide Peptidase Like 2a) is an intramembrane aspartyl protease engaged in the function of B-cells and dendritic cells. Despite being an attractive target for modulation of the immune system, selective SPPL2a inhibitors are barely described in the literature. Recently, we have disclosed a selective, small molecular weight agent SPL-707 which confirmed that pharmacological inhibition of SPPL2a leads to the accumulation of its substrate CD74/p8 and as a consequence to a reduction in the number of B-cells as well as myeloid dendritic cells in mice. In this paper we describe the discovery of novel hydroxyethylamine based SPPL2a inhibitors. Starting from a rather lipophilic screening hit, several iterative optimization cycles allowed for its transformation into a highly potent and selective compound 15 (SPL-410) which inhibited in vivo CD74/p8 fragment processing in mice at 10 mg/kg oral dose.

  DOI：

  10.1021/acsmedchemlett.9b00044
• 作为产物：
  描述：

  3-苯基缩水甘油 在 吡啶 、 sodium azide 、 氯化铵 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 37.0h， 生成 (2S,3S)-3-azido-2-((methylsulfonyl)oxy)-3-phenylpropyl pivalate
  参考文献：
  名称：

  Discovery of Orally Active Hydroxyethylamine Based SPPL2a Inhibitors

  摘要：

  SPPL2a (Signal Peptide Peptidase Like 2a) is an intramembrane aspartyl protease engaged in the function of B-cells and dendritic cells. Despite being an attractive target for modulation of the immune system, selective SPPL2a inhibitors are barely described in the literature. Recently, we have disclosed a selective, small molecular weight agent SPL-707 which confirmed that pharmacological inhibition of SPPL2a leads to the accumulation of its substrate CD74/p8 and as a consequence to a reduction in the number of B-cells as well as myeloid dendritic cells in mice. In this paper we describe the discovery of novel hydroxyethylamine based SPPL2a inhibitors. Starting from a rather lipophilic screening hit, several iterative optimization cycles allowed for its transformation into a highly potent and selective compound 15 (SPL-410) which inhibited in vivo CD74/p8 fragment processing in mice at 10 mg/kg oral dose.

  DOI：

  10.1021/acsmedchemlett.9b00044

文献信息

• Enantioselective synthesis of (+)-l-733,060
  作者：Shijo K. Cherian、Pradeep Kumar

  DOI：10.1016/j.tetasy.2007.04.006

  日期：2007.5

  An efficient enantioselective synthesis of (+)-L-733,060 from cinnamyl alcohol is described. The key steps include a Sharpless asymmetric epoxidation, a regioselective allyl opening of an epoxide and piperidine ring formation via a one pot Staudinger/aza-Wittig reaction. (c) 2007 Elsevier Ltd. All rights reserved.