tert-butyl (2R)-2-[(1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl]-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

• 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 (2R)-2-[(1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl]-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate
• 英文别名: tert-Butyl(2R)-2-((1R,2S)-2-methoxy-2-methyl-1-(acetylamino)pentyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate；tert-butyl (2R)-2-[(1R,2S)-1-acetamido-2-methoxy-2-methylpentyl]-5-oxo-2H-pyrrole-1-carboxylate
• 化学式: C₁₈H₃₀N₂O₅
• 分子量: 354.447
• InChiKey: BFECAJNMDWNFHZ-SIIHOXLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2E)-2-methyl-2-penten-1-ol 在 4 A molecular sieve titanium(IV) isopropylate 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 D-(-)-酒石酸二甲酯 、 4 A molecular sieve 、 Celite 、 三氟化硼乙醚 、 氨 、 氢气 、 sodium hexamethyldisilazane 、 sodium hydride 、 silver nitrate 、 三乙胺 、 pyridinium chlorochromate 、 三甲氧基磷 作用下， 以 四氢呋喃 、 甲醇 、 癸烷 、 二氯甲烷 为溶剂， 反应 64.75h， 生成 tert-butyl (2R)-2-[(1R,2S)-1-(acetylamino)-2-methoxy-2-methylpentyl]-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

• US6455571B1
  申请人：——

  公开号：US6455571B1

  公开（公告）日：2002-09-24
• 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.