(R)-2-[(S)-hydroxy-((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)methyl]piperidine-1-carboxylic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (R)-2-[(S)-hydroxy-((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)methyl]piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2R)-2-[(S)-[(2S,5R)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]-hydroxymethyl]piperidine-1-carboxylate
• 化学式: C₂₀H₃₅N₃O₅
• 分子量: 397.515
• InChiKey: BLSXKZNXOGSYIQ-WCVJEAGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  93
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-2-[(S)-hydroxy-((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)methyl]piperidine-1-carboxylic acid tert-butyl ester 在 盐酸 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以58%的产率得到(R)-2-[(S)-2-amino-(R)-1-hydroxy-2-methoxycarbonylethyl]piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective synthesis of β-hydroxy-α-amino acids β-substituted with non-aromatic heterocycles

  摘要：

  We have stereo selectively synthesised P-hydroxy-a-amino acids beta-substituted with non-aromatic heterocycles by means of a condensation reaction between enantiomerically pure heterocyclic aldehydes and the (R)-(+)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (Schollkopf's reagent) as a chiral auxiliary. The stereocontrolled addition gave mixtures of diastereoisomers whose steric configurations were assigned on the basis of spectroscopic data and X-ray analysis. Upon controlled hydrolysis, the adducts were transformed into the corresponding methyl esters of beta-hydroxy-beta-heterocyclic substituted a-amino acids. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.040
• 作为产物：
  描述：

  (R)-2,5-二氢-3,6-二甲氧基-2-异丙基吡嗪 、 (R)-2-甲酰基-1-哌啶甲酸叔丁酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.75h， 以40%的产率得到(R)-2-[(R)-hydroxy-((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)methyl]piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective synthesis of β-hydroxy-α-amino acids β-substituted with non-aromatic heterocycles

  摘要：

  We have stereo selectively synthesised P-hydroxy-a-amino acids beta-substituted with non-aromatic heterocycles by means of a condensation reaction between enantiomerically pure heterocyclic aldehydes and the (R)-(+)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (Schollkopf's reagent) as a chiral auxiliary. The stereocontrolled addition gave mixtures of diastereoisomers whose steric configurations were assigned on the basis of spectroscopic data and X-ray analysis. Upon controlled hydrolysis, the adducts were transformed into the corresponding methyl esters of beta-hydroxy-beta-heterocyclic substituted a-amino acids. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.040

文献信息

• Stereoselective synthesis of β-hydroxy-α-amino acids β-substituted with non-aromatic heterocycles
  作者：Giuseppe Cremonesi、Piero Dalla Croce、Francesco Fontana、Alessandra Forni、Concetta La Rosa

  DOI：10.1016/j.tetasy.2007.05.040

  日期：2007.7

  We have stereo selectively synthesised P-hydroxy-a-amino acids beta-substituted with non-aromatic heterocycles by means of a condensation reaction between enantiomerically pure heterocyclic aldehydes and the (R)-(+)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (Schollkopf's reagent) as a chiral auxiliary. The stereocontrolled addition gave mixtures of diastereoisomers whose steric configurations were assigned on the basis of spectroscopic data and X-ray analysis. Upon controlled hydrolysis, the adducts were transformed into the corresponding methyl esters of beta-hydroxy-beta-heterocyclic substituted a-amino acids. (c) 2007 Elsevier Ltd. All rights reserved.