tert-butyl (2R,3S)-2-((1R,2S)-2-methoxy-2-methyl-1-{[(R)-(4-methylphenyl)sulfinyl]amino}pentyl)-5-oxo-3-[(1Z)-prop-1-enyl]pyrrolidine-1-carboxylate | 335693-12-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (2R,3S)-2-((1R,2S)-2-methoxy-2-methyl-1-{[(R)-(4-methylphenyl)sulfinyl]amino}pentyl)-5-oxo-3-[(1Z)-prop-1-enyl]pyrrolidine-1-carboxylate
• 英文别名: tert-butyl (2R,3S)-2-[(1R,2S)-2-methoxy-2-methyl-1-[[(R)-(4-methylphenyl)sulfinyl]amino]pentyl]-5-oxo-3-[(Z)-prop-1-enyl]pyrrolidine-1-carboxylate
• CAS: 335693-12-4
• 化学式: C₂₆H₄₀N₂O₅S
• 分子量: 492.68
• InChiKey: BXDBUBXBJSBRTR-WWOTWPSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 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 (2R,3S)-2-((1R,2S)-2-methoxy-2-methyl-1-{[(R)-(4-methylphenyl)sulfinyl]amino}pentyl)-5-oxo-3-[(1Z)-prop-1-enyl]pyrrolidine-1-carboxylate 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 二异丁基氢化铝 、 三氟乙酸 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.48h， 生成 tert-butyl (2R,3S,5R)-2-[(1R,2S)-1-amino-2-methoxy-2-methylpentyl]-5-cyano-3-[(Z)-prop-1-enyl]pyrrolidine-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
• 作为产物：
  描述：

  4-Methyl-benzenesulfinic acid [(S)-2-methoxy-2-methyl-pent-(E)-ylidene]-amide 在 copper(I) bromide dimethylsulfide complex 、 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.17h， 生成 tert-butyl (2R,3S)-2-((1R,2S)-2-methoxy-2-methyl-1-{[(R)-(4-methylphenyl)sulfinyl]amino}pentyl)-5-oxo-3-[(1Z)-prop-1-enyl]pyrrolidine-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