ethyl (2S,3R,4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate | 135500-35-5

• 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-hydroxy-2-methylpropanoate
• 英文别名: tert-butyl (2S)-2-[(1R,2S)-3-ethoxy-1-hydroxy-2-methyl-3-oxopropyl]pyrrolidine-1-carboxylate
• CAS: 135500-35-5
• 化学式: C₁₅H₂₇NO₅
• 分子量: 301.383
• InChiKey: IDEZMCNLVGVMRL-SDDRHHMPSA-N

物化性质

• 沸点：
  408.9±15.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 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-hydroxy-2-methylpropanoate 在 盐酸 、 甲醇 、 lithium hydroxide 、 氢溴酸 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 溶剂黄146 、 三乙胺 、 焦碳酸二乙酯 、 lithium hexamethyldisilazane 、 lithium diisopropyl amide 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 202.0h， 生成 (S)-2-((S)-2-(二甲基氨基)-3-甲基丁酰氨基)-N-((3R,4S,5S)-3-甲氧基-1-((s)-2-((1R,2R)-1-甲氧基-2-甲基-3-氧代-3-(((S)-2-苯基-1-(噻唑-2-基）乙基)氨基)丙基)吡咯烷-1-基)-5-甲基-1-氧代庚烷-4-基)-N,3-二甲基丁酰胺
  参考文献：
  名称：

  An expeditious synthesis of dolastatin 10

  摘要：

  Total synthesis of dolastatin 10 (1) was completed by developing an efficient synthesis of two key amino acid components, Dil (6) and Dap (11), and subsequent stepwise coupling of five amino acid components from C-terminal Doe.

  DOI：

  10.1016/s0040-4039(00)79932-1
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以70%的产率得到ethyl (2S,3R,4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate
  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

• 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.
• An expeditious synthesis of dolastatin 10
  作者：Kiyoshi Tomioka、Motomu Kanai、Kenji Koga

  DOI：10.1016/s0040-4039(00)79932-1

  日期：1991.5

  Total synthesis of dolastatin 10 (1) was completed by developing an efficient synthesis of two key amino acid components, Dil (6) and Dap (11), and subsequent stepwise coupling of five amino acid components from C-terminal Doe.
• 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.