(4S)-1-(tert-butoxycarbonyl)-4-hydroxy-L-proline benzyl ester | 132622-90-3

• 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-hydroxy-L-proline benzyl ester
• 英文别名: N-tert-butoxycarbonyl-(2S,4S)-4-hydroxyproline benzyl ester；Boc-(4S)-cis-hydroxyproline benzyl；(2S,4S)-2-benzyl 1-tert-butyl 4-hydroxypyrrolidine-1,2-dicarboxylate；N-tert-butyloxycarbonyl-(2S,4S)-hydroxyproline benzyl ester；N-α-t-butoxycarbonyl cis-4-hydroxy-L-proline Benzyl Ester；Benzyl (4S)-1-Boc-4-hydroxy-L-prolinate；2-O-benzyl 1-O-tert-butyl (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate
• CAS: 132622-90-3
• 化学式: C₁₇H₂₃NO₅
• 分子量: 321.373
• InChiKey: BEIPCYKSYYZEJH-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-1-(tert-butoxycarbonyl)-4-hydroxy-L-proline benzyl ester 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 22.0~55.0 ℃ 、3.1 MPa 条件下， 生成 (2S,4s)-4-(氨基甲基)-1-(叔丁氧基羰基)吡咯烷-2-羧酸
  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：

  甘氨酸苄酯对甲苯磺酸盐 在 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 44.67h， 生成 (4S)-1-(tert-butoxycarbonyl)-4-hydroxy-L-proline benzyl ester
  参考文献：
  名称：

  A short diastereoselective synthesis of cis-(2S,4S) and cis-(2R,4R)-4-hydroxyprolines

  摘要：

  A concise synthesis of (2R,4R)-4-hydroxyproline (1) and (2,5,45)-4-hydroxyproline (2) has been developed in enantiomerically pure form from commercially available starting materials with excellent diastereoselectivity. The tightly bound chelation controlled transition state formed during the 5-exo-tet ring closure reaction is assumed to be the origin of high diastereoselectivity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.03.119

文献信息

• [EN] COMBINATIONS OF HEPATITIS C VIRUS INHIBITORS<br/>[FR] ASSOCIATIONS D'INHIBITEURS DU VIRUS DE L'HÉPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2015005901A1

  公开（公告）日：2015-01-15

  The present disclosure is generally directed to antiviral compounds, and more specifically directed to combinations of compounds which can inhibit the function of the NS5A protein encoded by Hepatitis C virus (HCV), compositions comprising such combinations, and methods for inhibiting the function of the NS5A protein.

  本公开涉及抗病毒化合物，更具体地涉及能够抑制由丙型肝炎病毒（HCV）编码的NS5A蛋白功能的化合物组合，包括这种组合的组合物，以及抑制NS5A蛋白功能的方法。
• [EN] FLUOROHYDROXYPROLINE DERIVATIVES USEFUL IN THE PREPARATION OF PROTEOLYSIS TARGETED CHIMERAS<br/>[FR] DÉRIVÉS DE FLUOROHYDROXYPROLINE UTILES DANS LA PRÉPARATION DE CHIMÈRES CIBLÉES PAR PROTÉOLYSE
  申请人：UNIV DUNDEE

  公开号：WO2018051107A1

  公开（公告）日：2018-03-22

  There is provided novel small molecule E3 ubiquitin ligase protein binding ligand compounds, and to their utility in PROteolysis Targeted Chimeras (PROTACs), as well as processes for their preparation thereof, and use in medicine. There is particularly provided novel small molecule E3 ubiquitin ligase protein binding inhibitorcompounds based on a fluorohydroxyproline scaffold, to their utility as ligands in synthesizing novel PROTACs, and to synthetic methods therefor.

  提供了新型小分子E3泛素连接酶蛋白结合配体化合物，以及它们在蛋白质降解靶向嵌合物（PROTACs）中的用途，以及其制备的过程，以及在医学中的用途。特别提供了基于氟羟脯氨酸支架的新型小分子E3泛素连接酶蛋白结合抑制剂化合物，以及它们作为配体在合成新型PROTACs中的用途，以及用于此目的的合成方法。
• Hepatitis C Virus Inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US20130183269A1

  公开（公告）日：2013-07-18

  The present disclosure is generally directed to antiviral compounds, and more specifically directed to combinations of compounds which can inhibit the function of the NS5A protein encoded by Hepatitis C virus (HCV), compositions comprising such combinations, and methods for inhibiting the function of the NS5A protein.

  本公开涉及抗病毒化合物，更具体地涉及能够抑制丙型肝炎病毒（HCV）编码的NS5A蛋白功能的化合物组合，包括这种组合的组成物，以及抑制NS5A蛋白功能的方法。
• 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。
• Novel peptides as NS3-serine protease inhibitors of hepatitis C virus
  申请人：——

  公开号：US20030216325A1

  公开（公告）日：2003-11-20

  The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.

  本发明公开了具有HCV蛋白酶抑制活性的新化合物，以及制备这种化合物的方法。在另一实施例中，本发明公开了包含这种化合物的药物组合物，以及使用它们治疗与HCV蛋白酶相关的疾病的方法。