(1E,2S)-2-methoxy-2-methylpentanal S-tritylthioxime | 471257-47-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (1E,2S)-2-methoxy-2-methylpentanal S-tritylthioxime
• 英文别名: (E,2S)-2-methoxy-2-methyl-N-tritylsulfanylpentan-1-imine
• CAS: 471257-47-3
• 化学式: C₂₆H₂₉NOS
• 分子量: 403.588
• InChiKey: DJBJUBMQBMLHND-KLFZOUAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1E,2S)-2-methoxy-2-methylpentanal S-tritylthioxime 在 三氟化硼乙醚 、 二异丁基氢化铝 、 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 9.42h， 生成 tert-butyl (2R,3S)-5-hydroxy-2-((1R,2S)-2-methoxy-2-methyl-1-((tritylthio)amino)pentyl)-3-((Z)-prop-1-en-1-yl)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：

  (2E)-2-methyl-2-penten-1-ol 在 4 A molecular sieve titanium(IV) isopropylate 、 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 D-(-)-酒石酸二甲酯 、 4 A molecular sieve 、 Celite 、 氢气 、 sodium hexamethyldisilazane 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 magnesium sulfate 、 三乙胺 、 pyridinium chlorochromate 、 三甲氧基磷 作用下， 以 四氢呋喃 、 乙醚 、 癸烷 、 二氯甲烷 为溶剂， 反应 60.5h， 生成 (1E,2S)-2-methoxy-2-methylpentanal S-tritylthioxime
  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

• Process for the preparation of substituted pyrrolidine neuraminidase inhibitors
  申请人：——

  公开号：US20030055297A1

  公开（公告）日：2003-03-20

  A process for the preparation of neuraminidase inhibitors having structural formula (28) 1 or therapeutically acceptable salts thereof, in which R 1 is alkyl, cycloalkyl, cycloalkylalkyl, or arylalkyl; R 2 is alkyl, cycloalkyl, cycloalkylalkyl, or arylalkyl; R 4 is alkyl, cycloalkyalkyl, or aryl-(C 2 -C 4 -alkyl); R 10 is methyl, ethyl, iso-propyl, or vinyl; and R 12 is hydrogen or alkyl and intermediates useful for the process are disclosed.

  一种用于制备具有结构式（28）1或其治疗上可接受的盐的神经氨酸酶抑制剂的方法，其中R1是烷基，环烷基，环烷基烷基或芳基烷基；R2是烷基，环烷基，环烷基烷基或芳基烷基；R4是烷基，环烷烷基或芳基（C2-C4-烷基）；R10是甲基，乙基，异丙基或乙烯基；和R12是氢或烷基，公开了用于该方法的中间体。
• 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.