(4R)-1-(tert-butoxycarbonyl)-4-cyano-D-proline ethyl ester | 132622-83-4

• 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: (4R)-1-(tert-butoxycarbonyl)-4-cyano-D-proline ethyl ester
• 英文别名: 1,2-Pyrrolidinedicarboxylic acid, 4-cyano-, 1-(1,1-dimethylethyl) 2-ethyl ester, (2R-cis)-；1-O-tert-butyl 2-O-ethyl (2R,4R)-4-cyanopyrrolidine-1,2-dicarboxylate
• CAS: 132622-83-4
• 化学式: C₁₃H₂₀N₂O₄
• 分子量: 268.313
• InChiKey: IPHOTSXAYLWNOY-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  79.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R)-1-(tert-butoxycarbonyl)-4-cyano-D-proline ethyl ester 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 22.0 ℃ 、3.1 MPa 条件下， 生成 (2R-顺式)-4-(氨基甲基)吡咯烷-1,2-二羧酸 1-叔丁酯
  参考文献：
  名称：

  Conformationally restricted arginine analogs

  摘要：

  We report the practical synthesis and structural characterization of a set of conformationally constrained protected arginine analogues. These enantiomerically pure analogues have the general structure 1 and are prepared in seven to eight steps from the commercially available isomers of 4-hydroxyproline. These analogues vary in side chain length and in relative and absolute stereochemistry and are suitable for the direct introduction into peptides. The resulting peptide analogues should be useful as enzymatically stable replacements for bioactive peptides and as probes for understanding the conformational aspects of protein-peptide interactions.

  DOI：

  10.1021/jo00009a016
• 作为产物：
  描述：

  N-α-tert-butyloxycarbonyl-cis-4-hydroxy-D-proline ethyl ester 在 四溴化碳 、 氰化四丁基铵 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 (4R)-1-(tert-butoxycarbonyl)-4-cyano-D-proline ethyl ester
  参考文献：
  名称：

  Conformationally restricted arginine analogs

  摘要：

  We report the practical synthesis and structural characterization of a set of conformationally constrained protected arginine analogues. These enantiomerically pure analogues have the general structure 1 and are prepared in seven to eight steps from the commercially available isomers of 4-hydroxyproline. These analogues vary in side chain length and in relative and absolute stereochemistry and are suitable for the direct introduction into peptides. The resulting peptide analogues should be useful as enzymatically stable replacements for bioactive peptides and as probes for understanding the conformational aspects of protein-peptide interactions.

  DOI：

  10.1021/jo00009a016

文献信息

• WEBB, THOMAS R.;EIGENBROT, CHARLES, J. ORG. CHEM., 56,(1991) N, C. 3009-3016
  作者：WEBB, THOMAS R.、EIGENBROT, CHARLES

  DOI：——

  日期：——
• US5120859A
  申请人：——

  公开号：US5120859A

  公开（公告）日：1992-06-09
• Conformationally restricted arginine analogs
  作者：Thomas R. Webb、Charles Eigenbrot

  DOI：10.1021/jo00009a016

  日期：1991.4

  We report the practical synthesis and structural characterization of a set of conformationally constrained protected arginine analogues. These enantiomerically pure analogues have the general structure 1 and are prepared in seven to eight steps from the commercially available isomers of 4-hydroxyproline. These analogues vary in side chain length and in relative and absolute stereochemistry and are suitable for the direct introduction into peptides. The resulting peptide analogues should be useful as enzymatically stable replacements for bioactive peptides and as probes for understanding the conformational aspects of protein-peptide interactions.