ethyl (3R,4S,5S)-4-azido-5-(methanesulfonyloxy)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate | 1201685-75-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: ethyl (3R,4S,5S)-4-azido-5-(methanesulfonyloxy)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate
• 英文别名: ethyl (3R,4S,5S)-4-azido-5-methylsulfonyloxy-3-pentan-3-yloxycyclohexene-1-carboxylate
• CAS: 1201685-75-7
• 化学式: C₁₅H₂₅N₃O₆S
• 分子量: 375.446
• InChiKey: PBWHBSSHGQDEPZ-RDBSUJKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl (3R,4S,5S)-4-azido-5-(methanesulfonyloxy)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 在 三丁基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (3R,4S,5S)-4-Amino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester
  参考文献：
  名称：

  Efficient Formal Synthesis of Oseltamivir Phosphate (Tamiflu) with Inexpensive d-Ribose as the Starting Material

  摘要：

  An efficient formal synthesis of oseltamivir phosphate (Tamiflu) has been achieved in 12 steps with use of the inexpensive and highly abundant D-ribose as the starting material. This concise alternative route does not utilize protecting groups and features the Introduction of 3-pentylidene ketal as the latent 3-pentyl ether, the use of a highly efficient RCM reaction to form the Tamiflu skeleton, and selective functional group manipulations.

  DOI：

  10.1021/ol9024716
• 作为产物：
  描述：

  在 sodium azide 作用下， 以 水 、 丙酮 为溶剂， 反应 4.0h， 以81 mg的产率得到ethyl (3R,4S,5S)-4-azido-5-(methanesulfonyloxy)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate
  参考文献：
  名称：

  Efficient Formal Synthesis of Oseltamivir Phosphate (Tamiflu) with Inexpensive d-Ribose as the Starting Material

  摘要：

  An efficient formal synthesis of oseltamivir phosphate (Tamiflu) has been achieved in 12 steps with use of the inexpensive and highly abundant D-ribose as the starting material. This concise alternative route does not utilize protecting groups and features the Introduction of 3-pentylidene ketal as the latent 3-pentyl ether, the use of a highly efficient RCM reaction to form the Tamiflu skeleton, and selective functional group manipulations.

  DOI：

  10.1021/ol9024716

文献信息

• Efficient Formal Synthesis of Oseltamivir Phosphate (Tamiflu) with Inexpensive <scp>d</scp>-Ribose as the Starting Material
  作者：Hiroshi Osato、Ian L. Jones、Anqi Chen、Christina L. L. Chai

  DOI：10.1021/ol9024716

  日期：2010.1.1

  An efficient formal synthesis of oseltamivir phosphate (Tamiflu) has been achieved in 12 steps with use of the inexpensive and highly abundant D-ribose as the starting material. This concise alternative route does not utilize protecting groups and features the Introduction of 3-pentylidene ketal as the latent 3-pentyl ether, the use of a highly efficient RCM reaction to form the Tamiflu skeleton, and selective functional group manipulations.