(1'S,3R)-4-(tert-butoxycarbonyl)-1-[1'-benzyloxymethyl-2'-hydroxyethyl]-3-benzyl-2-oxopiperazine | 1060662-67-0

• 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: (1'S,3R)-4-(tert-butoxycarbonyl)-1-[1'-benzyloxymethyl-2'-hydroxyethyl]-3-benzyl-2-oxopiperazine
• CAS: 1060662-67-0
• 化学式: C₂₆H₃₄N₂O₅
• 分子量: 454.566
• InChiKey: WGYKWWKQDDJJBD-XZOQPEGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  79.31
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (1'S)-4-(tert-butoxycarbonyl)-1-[1'-benzyloxymethyl-2'-hydroxyethyl]-2-oxopiperazine 、 溴甲苯 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 以86%的产率得到(1'S,3R)-4-(tert-butoxycarbonyl)-1-[1'-benzyloxymethyl-2'-hydroxyethyl]-3-benzyl-2-oxopiperazine
  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