ethyl (3R,4S,5R)-3,4-O-thionyl-5-O-methanesulfonylshikimate | 1388051-82-8

• 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,5R)-3,4-O-thionyl-5-O-methanesulfonylshikimate
• 英文别名: ethyl (3aS,4R,7aR)-4-methylsulfonyloxy-2-oxo-3a,4,5,7a-tetrahydro-1,3,2lambda4-benzodioxathiole-6-carboxylate；ethyl (3aS,4R,7aR)-4-methylsulfonyloxy-2-oxo-3a,4,5,7a-tetrahydro-1,3,2λ4-benzodioxathiole-6-carboxylate
• CAS: 1388051-82-8
• 化学式: C₁₀H₁₄O₈S₂
• 分子量: 326.348
• InChiKey: PFFFPAAABCFTDE-JBRZAHBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl (3R,4S,5R)-3,4-O-thionyl-5-O-methanesulfonylshikimate 在 4-二甲氨基吡啶 、 sodium azide 、 三氟化硼乙醚 、 sodium hydride 、 氯化铵 、 三乙胺 、 三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.33h， 生成 5-叠氮奥塞米韦
  参考文献：
  名称：

  A novel and high-yielding asymmetric synthesis of oseltamivir phosphate (Tamiflu) starting from (−)-shikimic acid

  摘要：

  A novel and high-yielding asymmetric synthesis of oseltamivir phosphate 1 (Tamiflu(R)) is described. The target compound 1 was obtained in 55% overall yield via an 11-step asymmetric synthesis starting from the naturally abundant (-)-shikimic acid. The present synthesis is characterized by some advantages such as the easy separation of intermediate 6 from triphenylphosphine oxide by using its large water-solubility, the use of inexpensive reagents throughout the synthesis, the lack of toxic heavy metals, mild reaction conditions and high yields for all steps. The stereochemical structure of the key intermediate 6 was unequivocally confirmed by X-ray crystallographic analysis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.014
• 作为产物：
  描述：

  ethyl (3aS,4R,7aR)-4-hydroxy-2-oxo-3a,4,5,7a-tetrahydro-1,3,2lambda4-benzodioxathiole-6-carboxylate 、 甲基磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以96%的产率得到ethyl (3R,4S,5R)-3,4-O-thionyl-5-O-methanesulfonylshikimate
  参考文献：
  名称：

  A novel and high-yielding asymmetric synthesis of oseltamivir phosphate (Tamiflu) starting from (−)-shikimic acid

  摘要：

  A novel and high-yielding asymmetric synthesis of oseltamivir phosphate 1 (Tamiflu(R)) is described. The target compound 1 was obtained in 55% overall yield via an 11-step asymmetric synthesis starting from the naturally abundant (-)-shikimic acid. The present synthesis is characterized by some advantages such as the easy separation of intermediate 6 from triphenylphosphine oxide by using its large water-solubility, the use of inexpensive reagents throughout the synthesis, the lack of toxic heavy metals, mild reaction conditions and high yields for all steps. The stereochemical structure of the key intermediate 6 was unequivocally confirmed by X-ray crystallographic analysis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.014

文献信息

• A novel and high-yielding asymmetric synthesis of oseltamivir phosphate (Tamiflu) starting from (−)-shikimic acid
  作者：Liang-Deng Nie、Wei Ding、Xiao-Xin Shi、Na Quan、Xia Lu

  DOI：10.1016/j.tetasy.2012.05.014

  日期：2012.5

  A novel and high-yielding asymmetric synthesis of oseltamivir phosphate 1 (Tamiflu(R)) is described. The target compound 1 was obtained in 55% overall yield via an 11-step asymmetric synthesis starting from the naturally abundant (-)-shikimic acid. The present synthesis is characterized by some advantages such as the easy separation of intermediate 6 from triphenylphosphine oxide by using its large water-solubility, the use of inexpensive reagents throughout the synthesis, the lack of toxic heavy metals, mild reaction conditions and high yields for all steps. The stereochemical structure of the key intermediate 6 was unequivocally confirmed by X-ray crystallographic analysis. (C) 2012 Elsevier Ltd. All rights reserved.