tert-butyl (2R)-3-[(2S)-2-bromopropyl]sulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate | 1190770-55-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (2R)-3-[(2S)-2-bromopropyl]sulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1190770-55-8
• 化学式: C₁₅H₂₈BrNO₄S
• 分子量: 398.362
• InChiKey: AOHDMLQBDPGDKR-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R)-3-[(2S)-2-bromopropyl]sulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate 在 氨 作用下， 以 甲醇 为溶剂， 以70%的产率得到(R)-3-((R)-2-amino-1-methyl-ethylsulfanyl)-2-tert-butoxycarbonylamino-propionic acid tert-butyl ester
  参考文献：
  名称：

  Controlling thiiranium intermediates—a new route to an iNOS inhibitor

  摘要：

  Our synthetic efforts towards an iNOS (inducible isoform of the nitric oxide synthase) inhibitor led us to the relatively unexplored field of generating and controlling the reactivity of chiral, unsymmetrical thiiranium species. We found that product regiochemistry depends on a tunable equilibrium, the understanding of which proved pivotal in defining a new route to a drug substance. The development of a new amidination method is also discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.059
• 作为产物：
  描述：

  tert-butyl (2R)-3-[(2R)-1-hydroxypropan-2-yl]sulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate 在 甲基磺酰氯 、 三乙胺 、 lithium bromide 、 sodium bromide 作用下， 以 水 为溶剂， 反应 0.5h， 生成 tert-butyl (2R)-3-[(2S)-2-bromopropyl]sulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
  参考文献：
  名称：

  Controlling thiiranium intermediates—a new route to an iNOS inhibitor

  摘要：

  Our synthetic efforts towards an iNOS (inducible isoform of the nitric oxide synthase) inhibitor led us to the relatively unexplored field of generating and controlling the reactivity of chiral, unsymmetrical thiiranium species. We found that product regiochemistry depends on a tunable equilibrium, the understanding of which proved pivotal in defining a new route to a drug substance. The development of a new amidination method is also discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.059

文献信息

• Controlling thiiranium intermediates—a new route to an iNOS inhibitor
  作者：Geracimos Rassias、Stephen A. Hermitage

  DOI：10.1016/j.tetlet.2009.07.059

  日期：2009.10

  Our synthetic efforts towards an iNOS (inducible isoform of the nitric oxide synthase) inhibitor led us to the relatively unexplored field of generating and controlling the reactivity of chiral, unsymmetrical thiiranium species. We found that product regiochemistry depends on a tunable equilibrium, the understanding of which proved pivotal in defining a new route to a drug substance. The development of a new amidination method is also discussed. (C) 2009 Elsevier Ltd. All rights reserved.