methyl (2S)-3-benzyloxy-2-[4'-(tert-butoxycarbonyl)-1'-piperazinyl]propanoate | 1060662-49-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S)-3-benzyloxy-2-[4'-(tert-butoxycarbonyl)-1'-piperazinyl]propanoate
• 英文别名: tert-butyl 4-[(2S)-1-methoxy-1-oxo-3-phenylmethoxypropan-2-yl]piperazine-1-carboxylate
• CAS: 1060662-49-8
• 化学式: C₂₀H₃₀N₂O₅
• 分子量: 378.469
• InChiKey: KUJSKTXNVIMPJK-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  68.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S)-3-benzyloxy-2-[4'-(tert-butoxycarbonyl)-1'-piperazinyl]propanoate 在 ruthenium(IV) oxide sodium periodate 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 以58%的产率得到methyl (2S)-3-benzyloxy-2-[4'-(tert-butoxycarbonyl)-2'-oxopiperazin-1'-yl]propanoate
  参考文献：
  名称：

  New efficient enantioselective synthesis of 2-oxopiperazines: a practical access to chiral 3-substituted 2-oxopiperazines

  摘要：

  The development of efficient and stereoselective methods to produce 1,4-disubstituted-2-oxopiperazine in enantiomerically pure form, from a readily available starting material is crucial. Herein, we report a reduction modification to our previously described synthesis of 1,4-disubstituted-2-oxopiperazine and also two original shortly accessed pathways. These new pathways can be routinely performed on a multigram scale and should rapidly find a place in the preparation of the 3-substituted-2-oxopiperazine diastereomers. Stereoselective alkylation of 1,4-disubstituted-2-oxopiperazine led to the corresponding (3S)-diastereomer or (3R)-diastereomer from the corresponding 2-oxopiperazine enantiomer with the chiral inductor substituted at the N-1 (1*) position, respectively, in good yield. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.030
• 作为产物：
  描述：

  甲基3-O-苄基-D-甘油酸盐 、 N-Boc-哌嗪 在 三氟甲磺酸酐 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以98%的产率得到methyl (2S)-3-benzyloxy-2-[4'-(tert-butoxycarbonyl)-1'-piperazinyl]propanoate
  参考文献：
  名称：

  New efficient enantioselective synthesis of 2-oxopiperazines: a practical access to chiral 3-substituted 2-oxopiperazines

  摘要：

  The development of efficient and stereoselective methods to produce 1,4-disubstituted-2-oxopiperazine in enantiomerically pure form, from a readily available starting material is crucial. Herein, we report a reduction modification to our previously described synthesis of 1,4-disubstituted-2-oxopiperazine and also two original shortly accessed pathways. These new pathways can be routinely performed on a multigram scale and should rapidly find a place in the preparation of the 3-substituted-2-oxopiperazine diastereomers. Stereoselective alkylation of 1,4-disubstituted-2-oxopiperazine led to the corresponding (3S)-diastereomer or (3R)-diastereomer from the corresponding 2-oxopiperazine enantiomer with the chiral inductor substituted at the N-1 (1*) position, respectively, in good yield. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.030

文献信息

• New efficient enantioselective synthesis of 2-oxopiperazines: a practical access to chiral 3-substituted 2-oxopiperazines
  作者：Claiton Leoneti Lencina、Alexandra Dassonville-Klimpt、Pascal Sonnet

  DOI：10.1016/j.tetasy.2008.06.030

  日期：2008.7

  The development of efficient and stereoselective methods to produce 1,4-disubstituted-2-oxopiperazine in enantiomerically pure form, from a readily available starting material is crucial. Herein, we report a reduction modification to our previously described synthesis of 1,4-disubstituted-2-oxopiperazine and also two original shortly accessed pathways. These new pathways can be routinely performed on a multigram scale and should rapidly find a place in the preparation of the 3-substituted-2-oxopiperazine diastereomers. Stereoselective alkylation of 1,4-disubstituted-2-oxopiperazine led to the corresponding (3S)-diastereomer or (3R)-diastereomer from the corresponding 2-oxopiperazine enantiomer with the chiral inductor substituted at the N-1 (1*) position, respectively, in good yield. (C) 2008 Elsevier Ltd. All rights reserved.