(4S)-1-(tert-butoxycarbonyl)-4-chloro-L-proline ethyl ester | 132622-64-1

• 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: (4S)-1-(tert-butoxycarbonyl)-4-chloro-L-proline ethyl ester
• 英文别名: 1-O-tert-butyl 2-O-ethyl (2S,4S)-4-chloropyrrolidine-1,2-dicarboxylate
• CAS: 132622-64-1
• 化学式: C₁₂H₂₀ClNO₄
• 分子量: 277.748
• InChiKey: QVOBWEGBSVLOKR-IUCAKERBSA-N

物化性质

• 沸点：
  347.8±42.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-1-(tert-butoxycarbonyl)-4-chloro-L-proline ethyl ester 在 sodium hydroxide 、 sodium azide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 生成 (2S,4R)-4-azido-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid
  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：

  1-叔丁氧羰基-(4R)-羟基-2-脯氨酸乙脂 在 四氯化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以76%的产率得到(4S)-1-(tert-butoxycarbonyl)-4-chloro-L-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
• 作为试剂：
  描述：

  2-benzyl 1-tert-butyl (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate 、 四溴化碳 、 三苯基膦 在 (4S)-1-(tert-butoxycarbonyl)-4-chloro-L-proline ethyl ester 作用下， 以 二氯甲烷 为溶剂， 反应 18.17h， 生成 (4S)-1-(tert-butoxycarbonyl)-4-bromo-D-proline benzyl ester
  参考文献：
  名称：

  Chimeric amino acid analogues

  摘要：

  提供了一种嵌入肽中的嵌合氨基酸类似物，该化合物由公式1表示：##STR1##其中，P.sub.1最好是氨基保护剂，P.sub.2和P.sub.3最好是氨基或鸟嘌呤保护剂。X可以是OH、卤素或更好的活化基团，适合通过常规手段将公式1化合物与肽结合，m和n分别为0-1和0-2。提供了含有嵌合氨基酸类似物的肽，其中包括一个由Aaa.sub.1-CPdl-Gly-Asp-Aaa.sub.2表示的血小板聚集抑制剂，其中Aaa.sub.1是Gly或H，Cpdl是已去保护的公式1化合物，Aaa.sub.2是一个亲水性氨基酸，最好是Val。

  公开号：

  US05120859A1

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
• Chimeric amino acid analogues
  申请人：Genentech, Inc.

  公开号：US05120859A1

  公开（公告）日：1992-06-09

  A chimeric amino acid analogue is provided suitable for incorporating into peptides which compound is represented by Formula 1: ##STR1## where P.sub.1 is preferably an amine protecting agent, and P.sub.2 and P.sub.3 are preferably amine or guanidine protecting agents. X can be OH, halide, or preferably an activating group suitable for conjugating the compound of Formula 1 to a peptide by conventional means, and m and n are 0-1 and 0-2 respectively. Peptides containing the chimeric amino acid analog are provided and include a platelet-aggregation inhibitor represented by Aaa.sub.1 -CPdl-Gly-Asp-Aaa.sub.2 where Aaa.sub.1 is Gly or H, Cpdl is the compound of Formula 1 which has been deprotected and Aaa.sub.2 is a hydrophobic amino acid preferably Val.

  提供了一种适合用于合成肽中的嵌合氨基酸类似物，该化合物由以下式表示：##STR1## 其中P.sub.1 最好是氨基保护剂，P.sub.2 和P.sub.3 最好是氨基或胍啉保护剂。X 可以是OH、卤素，或者最好是适合通过常规手段与Formula 1化合物结合的活化基团，m 和n 分别为0-1和0-2。提供了含有嵌合氨基酸类似物的肽，并包括一个由Aaa.sub.1 -CPdl-Gly-Asp-Aaa.sub.2 表示的血小板聚集抑制剂，其中Aaa.sub.1 是Gly或H，Cpdl 是已去保护的Formula 1化合物，Aaa.sub.2 是一个疏水性氨基酸，最好是Val。
• 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.