tert-butyl (2S)-2-((1S,2S)-2-methoxy-2-methyl-1-{[(S)-(4-methylphenyl)sulfinyl]amino}pentyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate | 408505-19-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: tert-butyl (2S)-2-((1S,2S)-2-methoxy-2-methyl-1-{[(S)-(4-methylphenyl)sulfinyl]amino}pentyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate
• 英文别名: tert-butyl (2S)-2-[(1S,2S)-2-methoxy-2-methyl-1-[[(S)-(4-methylphenyl)sulfinyl]amino]pentyl]-5-oxo-2H-pyrrole-1-carboxylate
• CAS: 408505-19-1
• 化学式: C₂₃H₃₄N₂O₅S
• 分子量: 450.599
• InChiKey: SKJKKEOOAAXQRZ-RXEUEYBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-((1S,2S)-2-methoxy-2-methyl-1-{[(S)-(4-methylphenyl)sulfinyl]amino}pentyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate 生成
  参考文献：
  名称：

  Enantioselective Synthesis of Antiinfluenza Compound A-315675

  摘要：

  Drug discovery efforts at Abbott Laboratories have led to the identification of influenza neuraminidase inhibitor A-315675 (1) as a candidate for development as an antiinfluenza drug. A convergent, stereoselective synthesis of this highly functionalized pyrrolidine is reported that utilizes pyrrolinone 2 as the key intermediate. The C5, C6 stereochemistry was established through a diastereoselective condensation of chiral imine compound 3 with silyloxypyrrole 4 to give pyrrolinone 2. The stereochemical outcome of this reaction depended critically on the choice of the imine functional group (FG), with tritylsulfenyl and (R)-toluenesulfinyl providing the desired products in good yields as crystalline intermediates. Conversion of pyrrolinone 2 into 1 was accomplished in seven subsequent steps, including Michael addition of cis-1-propenylcuprate at C4 and introduction of a cyano group as a carboxylic acid equivalent at C2.

  DOI：

  10.1021/jo0162890
• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole 、 4-Methyl-benzenesulfinic acid [(S)-2-methoxy-2-methyl-pent-(E)-ylidene]-amide 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以61%的产率得到tert-butyl (2S)-2-((1S,2S)-2-methoxy-2-methyl-1-{[(S)-(4-methylphenyl)sulfinyl]amino}pentyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate
  参考文献：
  名称：

  Enantioselective Synthesis of Antiinfluenza Compound A-315675

  摘要：

  Drug discovery efforts at Abbott Laboratories have led to the identification of influenza neuraminidase inhibitor A-315675 (1) as a candidate for development as an antiinfluenza drug. A convergent, stereoselective synthesis of this highly functionalized pyrrolidine is reported that utilizes pyrrolinone 2 as the key intermediate. The C5, C6 stereochemistry was established through a diastereoselective condensation of chiral imine compound 3 with silyloxypyrrole 4 to give pyrrolinone 2. The stereochemical outcome of this reaction depended critically on the choice of the imine functional group (FG), with tritylsulfenyl and (R)-toluenesulfinyl providing the desired products in good yields as crystalline intermediates. Conversion of pyrrolinone 2 into 1 was accomplished in seven subsequent steps, including Michael addition of cis-1-propenylcuprate at C4 and introduction of a cyano group as a carboxylic acid equivalent at C2.

  DOI：

  10.1021/jo0162890

文献信息

• Enantioselective Synthesis of Antiinfluenza Compound A-315675
  作者：David A. DeGoey、Hui-Ju Chen、William J. Flosi、David J. Grampovnik、Clinton M. Yeung、Larry L. Klein、Dale J. Kempf

  DOI：10.1021/jo0162890

  日期：2002.8.1

  Drug discovery efforts at Abbott Laboratories have led to the identification of influenza neuraminidase inhibitor A-315675 (1) as a candidate for development as an antiinfluenza drug. A convergent, stereoselective synthesis of this highly functionalized pyrrolidine is reported that utilizes pyrrolinone 2 as the key intermediate. The C5, C6 stereochemistry was established through a diastereoselective condensation of chiral imine compound 3 with silyloxypyrrole 4 to give pyrrolinone 2. The stereochemical outcome of this reaction depended critically on the choice of the imine functional group (FG), with tritylsulfenyl and (R)-toluenesulfinyl providing the desired products in good yields as crystalline intermediates. Conversion of pyrrolinone 2 into 1 was accomplished in seven subsequent steps, including Michael addition of cis-1-propenylcuprate at C4 and introduction of a cyano group as a carboxylic acid equivalent at C2.