(2R,4R)-2-Benzyl-1-tert-butoxycarbonyl-4-hydroxy-pyrrolidine-2-carboxylic acid | 852633-13-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2R,4R)-2-Benzyl-1-tert-butoxycarbonyl-4-hydroxy-pyrrolidine-2-carboxylic acid
• 英文别名: (2R,4R)-2-benzyl-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
• CAS: 852633-13-7
• 化学式: C₁₇H₂₃NO₅
• 分子量: 321.373
• InChiKey: KHKOYPNNTMCNEG-CXAGYDPISA-N

物化性质

• 沸点：
  486.4±45.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,4R)-2-Benzyl-1-tert-butoxycarbonyl-4-hydroxy-pyrrolidine-2-carboxylic acid 在 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 三乙胺 作用下， 以 甲苯 为溶剂， 以66%的产率得到tert-butyl (1R,4R)-4-benzyl-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate
  参考文献：
  名称：

  Synthesis of 2,2-Disubstituted Pyrrolidine-4-carboxylic Acid Derivatives and Their Incorporation into β-Peptide Oligomers

  摘要：

  We have recently shown that members of a new class of P-peptides, containing 2,2-disubstituted pyrrolidine-4-carboxylic acid residues, display discrete conformational preferences despite the impossibility of internal hydrogen bonding (Huck et al. J. Am. Chem. Soc. 2003, 125, 9035). Here we describe the synthesis of a variety of 2,2-disubstituted pyrrolidine-4-carboxylic derivatives that bear a diverse set of side chains and protecting groups suitable for oligomer synthesis. In addition, we discuss coupling methods for construction of oligomers in solution and on solid phase. Nonhydrogen bonded foldamers such as those generated from 2,2-disubstituted pyrrolidine-4-carboxylic acids may be useful in biomedical applications because the low intrinsic polarity of their backbones may promote bioavailability.

  DOI：

  10.1021/jo048639z
• 作为产物：
  描述：

  N-Boc-反式-4-羟基-L-脯氨酸甲酯 在 咪唑 、 六甲基磷酰三胺 、 sodium hydroxide 、 正丁基锂 、 四丁基氟化铵 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,4R)-2-Benzyl-1-tert-butoxycarbonyl-4-hydroxy-pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of 2,2-Disubstituted Pyrrolidine-4-carboxylic Acid Derivatives and Their Incorporation into β-Peptide Oligomers

  摘要：

  We have recently shown that members of a new class of P-peptides, containing 2,2-disubstituted pyrrolidine-4-carboxylic acid residues, display discrete conformational preferences despite the impossibility of internal hydrogen bonding (Huck et al. J. Am. Chem. Soc. 2003, 125, 9035). Here we describe the synthesis of a variety of 2,2-disubstituted pyrrolidine-4-carboxylic derivatives that bear a diverse set of side chains and protecting groups suitable for oligomer synthesis. In addition, we discuss coupling methods for construction of oligomers in solution and on solid phase. Nonhydrogen bonded foldamers such as those generated from 2,2-disubstituted pyrrolidine-4-carboxylic acids may be useful in biomedical applications because the low intrinsic polarity of their backbones may promote bioavailability.

  DOI：

  10.1021/jo048639z

文献信息

• Synthesis of 2,2-Disubstituted Pyrrolidine-4-carboxylic Acid Derivatives and Their Incorporation into β-Peptide Oligomers
  作者：Bayard R. Huck、Samuel H. Gellman

  DOI：10.1021/jo048639z

  日期：2005.4.1

  We have recently shown that members of a new class of P-peptides, containing 2,2-disubstituted pyrrolidine-4-carboxylic acid residues, display discrete conformational preferences despite the impossibility of internal hydrogen bonding (Huck et al. J. Am. Chem. Soc. 2003, 125, 9035). Here we describe the synthesis of a variety of 2,2-disubstituted pyrrolidine-4-carboxylic derivatives that bear a diverse set of side chains and protecting groups suitable for oligomer synthesis. In addition, we discuss coupling methods for construction of oligomers in solution and on solid phase. Nonhydrogen bonded foldamers such as those generated from 2,2-disubstituted pyrrolidine-4-carboxylic acids may be useful in biomedical applications because the low intrinsic polarity of their backbones may promote bioavailability.