(3R,5R)-1-tert-butoxycarbonyl-5-hydroxypiperazic acid methyl ester

• 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: (3R,5R)-1-tert-butoxycarbonyl-5-hydroxypiperazic acid methyl ester
• 英文别名: 1-O-tert-butyl 3-O-methyl (3R,5R)-5-hydroxydiazinane-1,3-dicarboxylate
• 化学式: C₁₁H₂₀N₂O₅
• 分子量: 260.29
• InChiKey: BDSUDVVVYXTLOH-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (3R,5R)-1-benzoyl-5-(tert-butyldimethylsilyloxy)-hexahydropyridazine-3-carbonitrile 在 盐酸 、 对甲苯磺酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 77.0h， 生成 (3R,5R)-1-tert-butoxycarbonyl-5-hydroxypiperazic acid methyl ester
  参考文献：
  名称：

  The efficient synthesis of (3R,5R)-5-hydroxypiperazic acid and its diastereomer using Lewis acid-promoted diastereoselective Strecker synthesis

  摘要：

  The stereoselective synthesis of (3R,5R)-5-hydroxypiperazic acid, a component of naturally occurring antibiotic cyclodepsipeptides, and its diastereomer was achieved via the use of Lewis acid-promoted diastereoselective Strecker synthesis as a key step, in which an interesting stereochemical reversal of diastereoselectivity by the choice of Lewis acid catalyst was observed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.004

文献信息

• Progress toward the synthesis of piperazimycin A: exploration of the synthesis of γ-hydroxy and γ-chloropiperazic acids
  作者：J. Phillip Kennedy、John T. Brogan、Craig W. Lindsley

  DOI：10.1016/j.tetlet.2008.04.132

  日期：2008.6

  Employing Hamada's chemistry with MAOS optimization of several steps, an expedient route to key (3S,5S)- and (3R,5R)-gamma-hydroxy and (3R,5S)-gamma-chloropiperazic acids, was developed en route to a total synthesis of piperazimycin A. (C) 2008 Elsevier Ltd. All rights reserved.
• The efficient synthesis of (3R,5R)-5-hydroxypiperazic acid and its diastereomer using Lewis acid-promoted diastereoselective Strecker synthesis
  作者：Kazuishi Makino、Hang Jiang、Tatsuya Suzuki、Yasumasa Hamada

  DOI：10.1016/j.tetasy.2006.06.004

  日期：2006.7

  The stereoselective synthesis of (3R,5R)-5-hydroxypiperazic acid, a component of naturally occurring antibiotic cyclodepsipeptides, and its diastereomer was achieved via the use of Lewis acid-promoted diastereoselective Strecker synthesis as a key step, in which an interesting stereochemical reversal of diastereoselectivity by the choice of Lewis acid catalyst was observed. (c) 2006 Elsevier Ltd. All rights reserved.