ethyl (2R,3S,4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate | 796853-20-8

• 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 (2R,3S,4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate
• CAS: 796853-20-8
• 化学式: C₁₅H₂₇NO₅
• 分子量: 301.383
• InChiKey: IDEZMCNLVGVMRL-WOPDTQHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  76.07
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl (2R,3S,4S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate 在 1,8-双二甲氨基萘 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 51.5h， 生成 <1S-(1β,2β,7aα)>-Hexahydro-1-methoxy-2-methyl-3-oxo-1H-pyrrolizine
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tet.2004.07.043
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 在 三乙胺 作用下， 以 甲醇 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