奥司他韦杂质41 | 1443055-47-7

• 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
• 中文名称: 奥司他韦杂质41
• 英文名称: (3R,4S,5R)-ethyl 5-acetylamino-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate
• 英文别名: Ethyl (3R,4S,5R)-5-acetamido-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate；ethyl (3R,4S,5R)-5-acetamido-4-hydroxy-3-pentan-3-yloxycyclohexene-1-carboxylate
• CAS: 1443055-47-7
• 化学式: C₁₆H₂₇NO₅
• 分子量: 313.394
• InChiKey: XXASCENXARITQN-KFWWJZLASA-N

物化性质

• 沸点：
  490.0±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  奥司他韦杂质41 在 4-二甲氨基吡啶 、 磷酸 、 三氟化硼乙醚 、 sodium hydride 、 caesium carbonate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 、 mineral oil 为溶剂， 反应 11.95h， 生成 磷酸奥司他韦
  参考文献：
  名称：

  A novel azide-free asymmetric synthesis of oseltamivir phosphate (Tamiflu) starting from Roche’s epoxide

  摘要：

  A novel azide-free asymmetric synthesis of oseltamivir phosphate 1 (Tamiflu (R)) starting from Roche's epoxide is described. Roche epoxide 2 was converted into N-acetyl aminoalcohol 3 in 95% yield via a BF3 center dot OEt2-catalyzed epoxide-opening with acetonitrile as a nucleophile. Compound 3 was then transformed into a methanesulfonate 4 in 98% yield. Compound 4 was converted into aziridine 5 in 91% yield. Aziridine 5 was subsequently converted into oseltamivir phosphate 1 via two paths (a and b). In the path a, compound 5 underwent aziridine-opening with diallylamine as a nucleophile to afford compound 7 in 93% yield; compound 7 could then be converted into oseltamivir phosphate 1 in 88% yield. In path b, compound 5 underwent aziridine-opening with isopropyl 2,2,2-trichloroacetimidate as a nucleophile to afford compound 8 in 94% yield, which was then converted into oseltamivir phosphate 1 in 82% yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.04.016
• 作为产物：
  描述：

  乙腈 、 5-(戊烷-3-基氧基)-7-氧代-双环[4.1.0]庚-3-烯-3-羧酸乙酯 在 三氟化硼乙醚 、 水 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 41.17h， 以95%的产率得到奥司他韦杂质41
  参考文献：
  名称：

  A novel azide-free asymmetric synthesis of oseltamivir phosphate (Tamiflu) starting from Roche’s epoxide

  摘要：

  A novel azide-free asymmetric synthesis of oseltamivir phosphate 1 (Tamiflu (R)) starting from Roche's epoxide is described. Roche epoxide 2 was converted into N-acetyl aminoalcohol 3 in 95% yield via a BF3 center dot OEt2-catalyzed epoxide-opening with acetonitrile as a nucleophile. Compound 3 was then transformed into a methanesulfonate 4 in 98% yield. Compound 4 was converted into aziridine 5 in 91% yield. Aziridine 5 was subsequently converted into oseltamivir phosphate 1 via two paths (a and b). In the path a, compound 5 underwent aziridine-opening with diallylamine as a nucleophile to afford compound 7 in 93% yield; compound 7 could then be converted into oseltamivir phosphate 1 in 88% yield. In path b, compound 5 underwent aziridine-opening with isopropyl 2,2,2-trichloroacetimidate as a nucleophile to afford compound 8 in 94% yield, which was then converted into oseltamivir phosphate 1 in 82% yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.04.016