ethyl (3S,4R,5R)-3-azido-5-benzoyloxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate | 1149345-83-4

• 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: ethyl (3S,4R,5R)-3-azido-5-benzoyloxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate
• 英文别名: [(1R,5S,6R)-5-azido-3-ethoxycarbonyl-6-methylsulfonyloxycyclohex-3-en-1-yl] benzoate
• CAS: 1149345-83-4
• 化学式: C₁₇H₁₉N₃O₇S
• 分子量: 409.42
• InChiKey: JUZJGVJAXCOGJR-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl (3S,4R,5R)-3-azido-5-benzoyloxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate 在 三苯基膦 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以88%的产率得到ethyl (1S,5R,6S)-5-benzoyloxy-7-aza-bicyclo[4,1,0]hept-2-ene-3-carboxylate
  参考文献：
  名称：

  A novel asymmetric synthesis of oseltamivir phosphate (Tamiflu) from (−)-shikimic acid

  摘要：

  Oseltamivir phosphate 1 was synthesized starting from a readily available acetonide, that is, ethyl (3R,4S,5R)-3,4-O-isopropylidene shikimate 2, through a new route via 11 steps and in 44% overall yield. The synthesis described in this article is characterized by two particular steps: the highly regioselective and stereoselective facile nucleophilic replacement of an OMs by ail N-3 group at the C-3 position of ethyl (3R,4S,5R)-3,4-O-bismethanesulfonyl-5-0-benzoyl shikimate 5, and the mild ring-opening of an aziridine with 3-pentanol at the C-1 position of ethyl (1 S,5R,6S)-7-acetyl-5-benzoyloxy-7-azabicyclo[4,1,0]hept-2-ene-3-carboxylate 8. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.027
• 作为产物：
  描述：

  ethyl (3R,4R,5R)-5-O-benzoyl-3,4-O-bis(methanesulfonyl)shikimate 在 sodium azide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以95%的产率得到ethyl (3S,4R,5R)-3-azido-5-benzoyloxy-4-methanesulfonyloxy-cyclohex-1-ene-1-carboxylate
  参考文献：
  名称：

  A novel asymmetric synthesis of oseltamivir phosphate (Tamiflu) from (−)-shikimic acid

  摘要：

  Oseltamivir phosphate 1 was synthesized starting from a readily available acetonide, that is, ethyl (3R,4S,5R)-3,4-O-isopropylidene shikimate 2, through a new route via 11 steps and in 44% overall yield. The synthesis described in this article is characterized by two particular steps: the highly regioselective and stereoselective facile nucleophilic replacement of an OMs by ail N-3 group at the C-3 position of ethyl (3R,4S,5R)-3,4-O-bismethanesulfonyl-5-0-benzoyl shikimate 5, and the mild ring-opening of an aziridine with 3-pentanol at the C-1 position of ethyl (1 S,5R,6S)-7-acetyl-5-benzoyloxy-7-azabicyclo[4,1,0]hept-2-ene-3-carboxylate 8. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.027

文献信息

• Novel asymmetric synthesis of oseltamivir phosphate (Tamiflu) from (−)-shikimic acid via cyclic sulfite intermediates
  作者：Liang-Deng Nie、Xiao-Xin Shi、Na Quan、Fei-Feng Wang、Xia Lu

  DOI：10.1016/j.tetasy.2011.09.014

  日期：2011.9

  A novel asymmetric synthesis of oseltamivir phosphate 1 from the naturally abundant (−)-shikimic acid via 3,4-cyclic sulfite intermediate 3 (Scheme 1) is described. Target compound 1 was obtained in 39% overall yield from this nine-step synthesis, and the characteristic step of the synthesis is the regio- and stereospecific nucleophilic substitution with sodium azide at the allylic (C-3) position of

  描述了通过3,4-环亚硫酸盐中间体3从天然丰富的（-）ki草酸中合成新的磷酸奥司他韦1的不对称合成（方案1）。通过该九步合成，以39％的总收率获得了目标化合物1，合成的特征步骤是在3,4-环的烯丙基（C-3）位置用叠氮化钠进行区域和立体特异性亲核取代。亚硫酸盐3。由于来自未保护的二羟基叠氮化物4的直接氮丙啶形成的产率不令人满意，因此通过保护的3，4-环亚硫酸盐10和13改进了所建立的化合物7的两种制备方法。（方案2）已经开发。在这两种改进的制剂，化合物7由3,4-二环状亚硫酸酯得到3中以64％的7-步骤或62％总产率分别。
• A novel asymmetric synthesis of oseltamivir phosphate (Tamiflu) from (−)-shikimic acid
  作者：Liang-Deng Nie、Xiao-Xin Shi

  DOI：10.1016/j.tetasy.2008.11.027

  日期：2009.1

  Oseltamivir phosphate 1 was synthesized starting from a readily available acetonide, that is, ethyl (3R,4S,5R)-3,4-O-isopropylidene shikimate 2, through a new route via 11 steps and in 44% overall yield. The synthesis described in this article is characterized by two particular steps: the highly regioselective and stereoselective facile nucleophilic replacement of an OMs by ail N-3 group at the C-3 position of ethyl (3R,4S,5R)-3,4-O-bismethanesulfonyl-5-0-benzoyl shikimate 5, and the mild ring-opening of an aziridine with 3-pentanol at the C-1 position of ethyl (1 S,5R,6S)-7-acetyl-5-benzoyloxy-7-azabicyclo[4,1,0]hept-2-ene-3-carboxylate 8. (C) 2008 Elsevier Ltd. All rights reserved.