(R)-2-((tert-butoxycarbonyl)amino)-2-methyl-4-(3-methylthiophen-2-yl)but-3-en-1-yl hexanoate | 827344-10-5

• 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: (R)-2-((tert-butoxycarbonyl)amino)-2-methyl-4-(3-methylthiophen-2-yl)but-3-en-1-yl hexanoate
• CAS: 827344-10-5
• 化学式: C₂₁H₃₃NO₄S
• 分子量: 395.563
• InChiKey: YJAUEZCZOXVAFO-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  27.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-2-((tert-butoxycarbonyl)amino)-2-methyl-4-(3-methylthiophen-2-yl)but-3-en-1-yl hexanoate 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 12.33h， 生成 (R)-4-Methyl-4-(2-(3-methylthiophen-2-yl)ethyl)oxazolidin-2-one
  参考文献：
  名称：

  Asymmetric synthesis of α,α-disubstituted α-amino alcohol derivatives

  摘要：

  We herein report an asymmetric synthesis of alpha,alpha-disubstituted alpha-amino alcohol derivatives 3, key intermediates of a novel immunomodulator, using enzymatic desymmetrization of 2-alkyl-2-tert-butoxycarbonylamino-1,3-propanediols 1a and 1b. This method makes it possible to prepare a chiral analogue of FTY720 4. These synthetic procedures allow for a broad structure variation in order to evaluate structure-activity relationships and the mechanism of action for sphingosine 1-phosphate-1 (SIP1) receptor agonist. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.007
• 作为产物：
  描述：

  (2R)-tert-butoxycarbonylamino-3-n-hexanoyloxy-2-methyl-1-propanol 在 4 A molecular sieve 、 potassium tert-butylate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.83h， 生成 (R)-2-((tert-butoxycarbonyl)amino)-2-methyl-4-(3-methylthiophen-2-yl)but-3-en-1-yl hexanoate
  参考文献：
  名称：

  Asymmetric synthesis of α,α-disubstituted α-amino alcohol derivatives

  摘要：

  We herein report an asymmetric synthesis of alpha,alpha-disubstituted alpha-amino alcohol derivatives 3, key intermediates of a novel immunomodulator, using enzymatic desymmetrization of 2-alkyl-2-tert-butoxycarbonylamino-1,3-propanediols 1a and 1b. This method makes it possible to prepare a chiral analogue of FTY720 4. These synthetic procedures allow for a broad structure variation in order to evaluate structure-activity relationships and the mechanism of action for sphingosine 1-phosphate-1 (SIP1) receptor agonist. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.007