allyl L-phenylalaninate hydrochloride | 96039-19-9

• 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: allyl L-phenylalaninate hydrochloride
• 英文别名: H-L-Phe-Oall HCl；prop-2-enyl (2S)-2-amino-3-phenylpropanoate;hydrochloride
• CAS: 96039-19-9
• 化学式: C₁₂H₁₅NO₂*ClH
• 分子量: 241.718
• InChiKey: SNBCPTZYXIHMQG-MERQFXBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.32
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  allyl L-phenylalaninate hydrochloride 在 palladium dihydroxide 、 四(三苯基膦)钯 吗啉 、 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 氰基磷酸二乙酯 、 五氟苯基二苯基磷酸酯 、 氢气 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 98.0h， 生成 cyclo[Boc-(S)-Thr-(S)-Phe-(S)-Phs-(S)-Phe-(S)-N-Me-Tyr(TBS)-(S)-Ile]
  参考文献：
  名称：

  Synthetic studies of the cyclic depsipeptides bearing the 3-amino-6-hydroxy-2-piperidone (Ahp) unit. Total synthesis of the proposed structure of micropeptin T-20

  摘要：

  The first total synthesis of a cyclic depsipeptide possessing the 3-amino-6-hydroxy-2-piperidone (Ahp) unit was successfully IN achieved in a convergent manner by the oxidative construction of the Ahp unit at the later stage of the synthesis. This synthetic work provides data indicating that the structure of the target Ahp-depsipeptide, micropeptin T-20. should be re-examined. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.009
• 作为产物：
  描述：

  2-tert-butoxycarbonylamino-3-phenylpropionic acid allyl ester 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 1.5h， 生成 allyl L-phenylalaninate hydrochloride
  参考文献：
  名称：

  Synthetic studies of the cyclic depsipeptides bearing the 3-amino-6-hydroxy-2-piperidone (Ahp) unit. Total synthesis of the proposed structure of micropeptin T-20

  摘要：

  The first total synthesis of a cyclic depsipeptide possessing the 3-amino-6-hydroxy-2-piperidone (Ahp) unit was successfully IN achieved in a convergent manner by the oxidative construction of the Ahp unit at the later stage of the synthesis. This synthetic work provides data indicating that the structure of the target Ahp-depsipeptide, micropeptin T-20. should be re-examined. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.009

文献信息

• Progress toward the assembly of the bicyclic theonellamide skeleton
  作者：Jyoti P. Mukherjee、Joyeeta Roy、Chyree S. Batton、Saroj Yadav、Douglas Wong、Carol M. Taylor

  DOI：10.1016/j.tet.2020.131127

  日期：2020.4

  synthesized in solution. Each ring was formed independently, providing insights into protecting group limitations, side reactions, and the optimal order of events to approach the formation of the bicyclic system. Ultimately, an undecapeptide was prepared, with the eastern ring formed. The twelfth amino acid, an l-α-aminoadipic acid building block, was prepared and preliminary investigations into its attachment

  的正交保护的τ-histidinoalanine残余物通过旋光纯的Boc-的区域选择性烷基化，合成升与亲电子从的Fmoc-衍生的磺酰胺酯-His-OTCE（TCE =三氯乙基）d -Ser-OBn的 目的是合成一种非天然的theonellamide，并调用其他10个氨基酸的易于获得的变体。在溶液中合成了与“ theonellamide X”的东环和西环相对应的肽片段。每个环都是独立形成的，可深入了解保护基团的限制，副反应以及接近双环系统形成的最佳事件顺序。最终，制备了十一肽，形成了东环。第十二氨基酸，升制备了-α-氨基己二酸构件，并报道了其与十一肽的连接的初步研究。
• Peptide‐Chain Elongation Using Unprotected Amino Acids in a Micro‐Flow Reactor
  作者：Shinichiro Fuse、Koshiro Masuda、Yuma Otake、Hiroyuki Nakamura

  DOI：10.1002/chem.201903531

  日期：2019.11.27

  Conventional peptide synthesis requires a deprotection step after each amidation step, which decreases synthetic efficiency. Therefore, peptide synthesis using unprotected amino acids is considered an ideal approach. Here, we report peptide chain elongation using unprotected amino acids via a mixed carbonic anhydride. Micro-flow technology enabled rapid mixing of an organic layer containing a protected

  常规的肽合成在每个酰胺化步骤之后都需要脱保护步骤，这降低了合成效率。因此，使用未保护的氨基酸合成肽被认为是一种理想的方法。在这里，我们报告使用未保护的氨基酸通过混合碳酸酐的肽链延长。微流技术使含有受保护的氨基酸或二肽的有机层与含有未保护的氨基酸或二肽的水层快速混合，从而加速了所需的酰胺化反应，该方法成功地抑制了不良的消旋/表观异构化（≤0.4％）。以高到高的产率获得了各种二肽，三肽和四肽。这是有关肽链延长的第一篇报道，该报道使用廉价，非爆炸性的，
• Development of a new microwave-assisted cleavable backbone amide linker (BAL): a comparative study
  作者：Stijn Claerhout、Thibault Duchène、Dirk Tourwé、Erik V. Van der Eycken

  DOI：10.1039/b919365k

  日期：——

  A thorough comparative study to demonstrate the properties of a new microwave labile backbone amide linker is presented. A cyclic pentapeptide, cyclo(Trp-Gln-Gly-β-Ala-Phe), was used as a model and synthesized following 16 different conditions. The new backbone amide linker is stable towards acid and base at r.t., and can be cleaved at elevated temperature in trifluoroacetic acid under microwave irradiation

  进行了全面的比较研究，以证明新型微波不稳定骨架酰胺连接基的性质。环状五肽，环（Trp - Gln - Gly - β - Ala - Phe）用作模型，并在16个不同条件下进行合成。新的骨架酰胺连接基在室温下对酸和碱稳定，可以在高温下裂解。三氟乙酸 在微波辐射下，避免使用腐蚀性试剂，例如 高频。新的链接器与Boc- 也 Fmoc-策略并允许在从树脂上裂解环五肽之前在rt裂解酸不稳定的侧链保护基。
• [EN] MIP INHIBITORS<br/>[FR] INHIBITEURS DE MIP
  申请人：DMTC LTD

  公开号：WO2023178378A1

  公开（公告）日：2023-09-28

  The present disclosure generally relates to pipecolic acid derived compounds, in particular pipecolic acid derived compounds of Formula (I), and to formulations and compositions comprising the same. The present disclosure also relates to methods and uses of these compounds, compositions and/or formulations in treating and/or preventing a disease or condition mediated by a pathogen which is responsive to inhibition of macrophage infectivity potentiator (Mip) proteins, and/or a disease or condition mediated in which Mip protein is a virulence factor.

  本公开一般涉及哌啶醇酸衍生化合物，特别是式(I)的哌啶醇酸衍生化合物，以及包含这些化合物的制剂和组合物。本公开还涉及这些化合物、组合物和/或制剂在治疗和/或预防由病原体介导的疾病或病症中的方法和用途，病原体对巨噬细胞感染性增效剂（Mip）蛋白的抑制反应敏感，和/或Mip蛋白是毒力因子的疾病或病症介导。
• Synthesis of protected sugar-amino acid hybrid molecules as platform for further derivatization
  作者：Han Liu、Xuechen Li

  DOI：10.1016/j.tetlet.2012.10.042

  日期：2012.12

  The sugar-amino acid hybrid molecules with appropriate protecting groups were synthesized from sugar-derived lactones and ester of amino acids in five high yielding steps. The C-5 of the resultant hybrid molecule, upon selective deprotection, can be further derivatized to afford the linear depsipeptide. (C) 2012 Elsevier Ltd. All rights reserved.