ethyl (4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-oxo-2-methylpropanoate | 351521-59-0

• 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 (4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-oxo-2-methylpropanoate
• 英文别名: tert-butyl (2S)-2-(3-ethoxy-2-methyl-3-oxopropanoyl)pyrrolidine-1-carboxylate
• CAS: 351521-59-0
• 化学式: C₁₅H₂₅NO₅
• 分子量: 299.367
• InChiKey: ZASKAGBUBHJMCG-DTIOYNMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-oxo-2-methylpropanoate 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 氢气 作用下， 以 乙醇 为溶剂， 50.0 ℃ 、13.0 MPa 条件下， 反应 117.0h， 生成 ethyl (3R,4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methyl-propanoate
  参考文献：
  名称：

  通过钌催化的不对称氢化全合成dolastatin 10

  摘要：

  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）。

  DOI：

  10.1016/j.tet.2007.03.036

文献信息

• 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.
• Synthesis of both syn and anti diastereoisomers of Boc-dolaproine from (S)-proline through DKR using ruthenium-catalyzed hydrogenation: a dramatic role of N-protecting groups
  作者：Céline Mordant、Sébastien Reymond、Virginie Ratovelomanana-Vidal、Jean-Pierre Genêt

  DOI：10.1016/j.tet.2004.07.043

  日期：2004.10

  The natural (2R,3R)-Boc-dolaproine and its unnatural (2S,3S) diastereoisomer were synthesized involving as key transformation the Ru(II)-promoted hydrogenation of the beta-keto-alpha-methyl ester derived from (S)-N-Boc-proline. Interestingly, the asymmetric hydrogenation of this beta-keto ester N-protected as an amine hydrochloride salt, provided the corresponding anti (2S,3R)- and (2R,3S)-beta-hydroxy-alpha-methyl esters with significant level of selectivities through dynamic kinetic resolution. (C) 2004 Elsevier Ltd. All rights reserved.
• 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）。