ethyl (2S,3R,4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methyl-propanoate | 351535-96-1

• 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: ethyl (2S,3R,4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methyl-propanoate
• 英文别名: ethyl (2S,3R,4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methylpropanoate；tert-butyl (2S)-2-[(1R,2S)-3-ethoxy-1-methoxy-2-methyl-3-oxopropyl]pyrrolidine-1-carboxylate
• CAS: 351535-96-1
• 化学式: C₁₆H₂₉NO₅
• 分子量: 315.41
• InChiKey: KMDUKJDMSANBEZ-RWMBFGLXSA-N

物化性质

• 沸点：
  394.1±12.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (2S,3R,4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methyl-propanoate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 14.5h， 以80%的产率得到(2S,3R)-3-((S)-1-(叔丁氧基羰基)吡咯烷-2-基)-3-甲氧基-2-甲基丙酸
  参考文献：
  名称：

  Stereoselective Synthesis of iso-Dolaproine via Dynamic Kinetic Resolution

  摘要：

  [GRAPHCIS]An efficient multigram-scale synthesis of optically pure Boc-(2S,3R,4S)-iso-dolaproine is reported using dynamic kinetic resolution (DKR), The catalytic asymmetric hydrogenation of ethyl (4S)-3-(2 ' -pyrrolidinyl)-3-oxo-2-methyl propanoate hydrochloride using in situ generated Ru[(S)MeO-BIPHEP]Br-2 catalyst affords the anti beta -hydroxy alpha -methyl ester quantitatively, The two new stereogenic centers are simultaneously controlled with high diastereoselectivity.

  DOI：

  10.1021/ol015955g
• 作为产物：
  描述：

  trimethoxonium tetrafluoroborate 、 ethyl (2S,3R,4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate 在 Proton Sponge 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 22.0h， 以63%的产率得到ethyl (2S,3R,4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methyl-propanoate
  参考文献：
  名称：

  Stereoselective Synthesis of iso-Dolaproine via Dynamic Kinetic Resolution

  摘要：

  [GRAPHCIS]An efficient multigram-scale synthesis of optically pure Boc-(2S,3R,4S)-iso-dolaproine is reported using dynamic kinetic resolution (DKR), The catalytic asymmetric hydrogenation of ethyl (4S)-3-(2 ' -pyrrolidinyl)-3-oxo-2-methyl propanoate hydrochloride using in situ generated Ru[(S)MeO-BIPHEP]Br-2 catalyst affords the anti beta -hydroxy alpha -methyl ester quantitatively, The two new stereogenic centers are simultaneously controlled with high diastereoselectivity.

  DOI：

  10.1021/ol015955g

文献信息

• Total synthesis of dolastatin 10 through ruthenium-catalyzed asymmetric hydrogenations
  作者：Céline Mordant、Sébastien Reymond、Hitoshi Tone、Damien Lavergne、Ridha Touati、Bechir Ben Hassine、Virginie Ratovelomanana-Vidal、Jean-Pierre Genet

  DOI：10.1016/j.tet.2007.03.036

  日期：2007.7

  synthesis of dolastatin 10, a potent inhibitor of microtubule assembly, which displayed remarkable antineoplastic activity, is reported. Our synthetic approach was based upon ruthenium-promoted asymmetric hydrogenation of β-keto esters derived from (S)-Boc-proline and (S)-Boc-isoleucine for the construction of the two key units: (2R,3R)-Boc-dolaproine (Dap) and (3R)-Boc-dolaisoleucine (Dil).

  据报道，dolastatin 10（一种有效的微管组装抑制剂）的全合成，显示出显着的抗肿瘤活性。我们的合成方法是基于钌促进的（S）-Boc-脯氨酸和（S）-Boc-异亮氨酸衍生的β-酮酯的不对称氢化反应，用于构建两个关键单元：（2 R，3 R）- Boc-dolaproine（Dap）和（3 R）-Boc-dolaisoleucine（Dil）。
• Stereoselective Synthesis of <i>iso</i>-Dolaproine via Dynamic Kinetic Resolution
  作者：Damien Lavergne、Céline Mordant、Virginie Ratovelomanana-Vidal、Jean-Pierre Genet

  DOI：10.1021/ol015955g

  日期：2001.6.1

  [GRAPHCIS]An efficient multigram-scale synthesis of optically pure Boc-(2S,3R,4S)-iso-dolaproine is reported using dynamic kinetic resolution (DKR), The catalytic asymmetric hydrogenation of ethyl (4S)-3-(2 ' -pyrrolidinyl)-3-oxo-2-methyl propanoate hydrochloride using in situ generated Ru[(S)MeO-BIPHEP]Br-2 catalyst affords the anti beta -hydroxy alpha -methyl ester quantitatively, The two new stereogenic centers are simultaneously controlled with high diastereoselectivity.