(R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(4-fluoro-benzyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester | 852633-29-5

• 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: (R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(4-fluoro-benzyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
• CAS: 852633-29-5
• 化学式: C₂₄H₃₈FNO₅Si
• 分子量: 467.653
• InChiKey: UDNBEIMQXMACJW-PHSANKKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(4-fluoro-benzyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到tert-butyl (4R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[(4-fluorophenyl)methyl]-2-(hydroxymethyl)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
• 作为产物：
  描述：

  L-羟基脯氨酸 在 咪唑 、 六甲基磷酰三胺 、 sodium hydroxide 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 3.0h， 生成 (R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(4-fluoro-benzyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
  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