tert-butyl (2S,4R)-2-(3-azidopropyl)-4-[tert-butyl(dimethyl)silyl]oxy-2-(methoxymethyl)pyrrolidine-1-carboxylate | 852633-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (2S,4R)-2-(3-azidopropyl)-4-[tert-butyl(dimethyl)silyl]oxy-2-(methoxymethyl)pyrrolidine-1-carboxylate
• CAS: 852633-05-7
• 化学式: C₂₀H₄₀N₄O₄Si
• 分子量: 428.647
• InChiKey: VXGQZCMVZWXMKX-UZLBHIALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,4R)-2-(3-azidopropyl)-4-[tert-butyl(dimethyl)silyl]oxy-2-(methoxymethyl)pyrrolidine-1-carboxylate 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 18-冠醚-6 、 四丁基氟化铵 、 氢气 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 20.0~80.0 ℃ 、310.26 kPa 条件下， 反应 6.0h， 生成 (3S,5S)-5-(methoxymethyl)-5-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-1-phenylmethoxycarbonylpyrrolidine-3-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
• 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 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 正丁基锂 、 sodium azide 、 硼烷 、 三乙胺 、 二异丙胺 、 silver(l) oxide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 8.75h， 生成 tert-butyl (2S,4R)-2-(3-azidopropyl)-4-[tert-butyl(dimethyl)silyl]oxy-2-(methoxymethyl)pyrrolidine-1-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

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.