Boc-L-Tyr(tBu)-OMe | 30845-22-8

• 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: Boc-L-Tyr(tBu)-OMe
• 英文别名: methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-[4-(tert-butoxy)phenyl]propanoate；methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propanoate
• CAS: 30845-22-8
• 化学式: C₁₉H₂₉NO₅
• 分子量: 351.443
• InChiKey: QVUHDEMEVAIGOF-HNNXBMFYSA-N

物化性质

• 沸点：
  464.7±40.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-L-Tyr(tBu)-OMe 在 erbium(III) triflate 作用下， 以 甲醇 为溶剂， 反应 0.75h， 生成 Boc-L-酪氨酸甲酯
  参考文献：
  名称：

  生态可持续的三氟甲磺酸Er（III）催化叔丁基醚的形成和裂解

  摘要：

  提出了一种生态相容的方法，该方法允许形成或裂解醇和酚的叔丁基醚。该保护步骤在室温下在无溶剂条件下使用催化量的Er（OTf）3进行。催化剂易于从水相中回收并重复使用几次，而活性没有明显损失。所开发的脱保护步骤也是高度环保的，因为使用MW辐射可以非常快速地从甲醇中的醇和酚中去除叔丁基。 绿色化学-路易斯酸-保护基-叔丁基醚-微波加热

  DOI：

  10.1055/s-0030-1258332
• 作为产物：
  描述：

  Z-L-酪氨酸甲酯 在 palladium on activated charcoal 硫酸 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.5h， 生成 Boc-L-Tyr(tBu)-OMe
  参考文献：
  名称：

  Flexible and Convergent Total Synthesis of Cyclotheonamide B

  摘要：

  A convergent approach using two key intermediates, segment A [a L-proline-L-alpha-hydroxy-beta-homoarginine-D-phenylalanine (Pro-hArg-D-Phe) tripeptide] and segment B [a vinylogous L-tyrosine-L-2,3-diaminopropanoic acid (vTyr-Dpr) dipeptide], was developed for the synthesis of cyclotheonamide B (Scheme 1). The starting compound for the preparation of the hArg moiety 7, the predominant part of segment A, was N-alpha-(benzyloxycarbonyl)-N-omega , N(omega)'bis(tert-butyloxycarbonyl)-l-arginine methyl ester (15, Scheme 2), which was converted into the aldehyde 16 and subsequently homologated using [tris(methylthio)methyl]lithium as a carboxylic acid anion equivalent. Coupling with properly protected Pro and D-Phe derivatives gave smoothly the desired Pro-hArg-D-Phe tripeptide derivative 24. The key feature of segment B, i.e., the L-tyrosine-derived alpha,beta-unsaturated gamma-amino acid 4, was prepared by a Wadsworth-Emmons olefination of the aldehyde 29 (Scheme 3) derived from N-(tert-butyloxycarbonyl), O-tert-butyl-L-tyrosine methyl ester (28). Selective N-(tert-butyloxycarbonyl) removal in the presence of the aryl tert-butyl ether present in the fully protected segment B, i.e., 32, was achieved by treatment with trimethylsilyl triflate/2,6-lutidine to give vTyr-Dpr dipeptide derivative 34 in quantitative yield. Coupling of the key intermediates 24 and 34 using 2-(1H-benzotriazol-l-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) afforded the protected linear pentapeptide 35 in high yield (Scheme 4). Treatment of 35 with Pd(PPh3)(4)/morpholine resulted in simultaneous removal of the C-terminal allyl group and the N-terminal allyloxycarbonyl group to yield 36. Ring closure was effected under dilution conditions by treatment with TBTU/1-hydroxybenzotriazole/4-(dimethylamino and gave the protected cyclopentapeptide 37 in 61% yield. Oxidation of the hydroxyl group with Dess-Rlartin periodinane (24 h, 40 degrees C) in the presence of tert-butyl alcohol gave 38, which was then subjected to O,N-deprotection with trifluoroacetic acid/thioanisole. Subsequent HPLC purification afforded cyclotheonamide B in an overall yield of 1.8% in 17 steps.

  DOI：

  10.1021/jo961447m

文献信息

• Substrate-Directed Lewis-Acid Catalysis for Peptide Synthesis
  作者：Wataru Muramatsu、Tomohiro Hattori、Hisashi Yamamoto

  DOI：10.1021/jacs.9b03850

  日期：2019.8.7

  A Lewis-acid-catalyzed method for the substrate-directed formation of peptide bonds has been developed, and this powerful approach is utilized for the new "remote" activation of carboxyl groups under solvent-free conditions. The presented method has the following advantages: 1) the high-yielding peptide synthesis uses a tantalum catalyst for any amino acids; 2) the reaction proceeds without any racemization;

  一种路易斯酸催化的底物定向形成肽键的方法已经被开发出来，这种强大的方法被用于在无溶剂条件下对羧基进行新的“远程”活化。该方法具有以下优点：1）高产肽合成对任何氨基酸均使用钽催化剂；2) 反应进行时没有任何外消旋化；3）采用钛催化剂的新型底物导向化学连接适用于会聚肽合成。这些优势克服了经典肽合成中一些未解决的问题。
• Novel high affinity quinoline-based kinase ligands
  申请人：Deng Yongqi

  公开号：US20080045568A1

  公开（公告）日：2008-02-21

  Quinoline-based inhibitors of cyclin dependent kinase 2, compositions including the inhibitors, and methods of using the inhibitors and inhibitor compositions are described. The inhibitors and compositions including them are useful for treating disease or disease symptoms. The invention also provides for methods of making CDK-2 inhibitor compounds, methods of inhibiting CDK-2, and methods for treating disease or disease symptoms.

  基于喹啉的细胞周期蛋白依赖激酶2抑制剂，包括这些抑制剂的组合物，以及使用这些抑制剂和抑制剂组合物的方法。这些抑制剂和包括它们的组合物对治疗疾病或疾病症状有用。该发明还提供了制备CDK-2抑制剂化合物的方法，抑制CDK-2的方法，以及治疗疾病或疾病症状的方法。
• 噁二唑类和噻二唑类化合物及其制备方法和用途
  申请人：中国药科大学

  公开号：CN109824621A

  公开（公告）日：2019-05-31

  本发明公开了一种噁二唑类和噻二唑类化合物及其制备方法和用途，该类化合物如下式Ⅰ或式Ⅱ所示，本发明的噁二唑类或噻二唑类化合物或其药学上可接受的盐、消旋体、旋光异构体或溶剂化合物可以调控PD‑1/PD‑L1及VISTA信号通路，作为能够阻断PD‑1/PD‑L1及VISTA信号通路的双靶点免疫检查点抑制剂，可以应用在制备抗肿瘤药物中。
• On double bond isosters of the peptide bond; an enkephalin analogue
  作者：Michael M. Hann、Peter G. Sammes、Peter D. Kennewell、John B. Taylor

  DOI：10.1039/c39800000234

  日期：——

  A route to peptide analogues incorporating the replacement of an amide bond with a trans-carbon–carbon double bond is presented and applied to the synthesis of a Leu5–enkephalin analogue.

  提出了一种肽类似物的方法，该方法将酰胺键替换为反碳-碳双键，并被用于Leu 5-脑啡肽类似物的合成。
• Universal Peptidomimetics
  作者：Eunhwa Ko、Jing Liu、Lisa M. Perez、Genliang Lu、Amber Schaefer、Kevin Burgess

  DOI：10.1021/ja1071916

  日期：2011.1.26

  This paper concerns peptidomimetic scaffolds that can present side chains in conformations resembling those of amino acids in secondary structures without incurring excessive entropic or enthalpic penalties. Compounds of this type are referred to here as minimalist mimics. The core hypothesis of this paper is that small sets of such scaffolds can be designed to analogue local pairs of amino acids (including noncontiguous ones) in any secondary structure; i.e., they are universal peptidomimetics. To illustrate this concept, we designed a set of four peptidomimetic scaffolds. Libraries based on them were made bearing side chains corresponding to many of the protein-derived amino acids. Modeling experiments were performed to give an indication of kinetic and thermodynamic accessibilities of conformations that can mimic secondary structures. Together, peptidomimetics based on these four scaffolds can adopt conformations that resemble almost any combination of local amino acid side chains in any secondary structure. Universal peptidomimetics of this kind are likely to be most useful in the design of libraries for high-throughput screening against diverse targets. Consequently, data arising from submission of these molecules to the NIH Molecular Libraries Small Molecule Repository (MLSMR) are outlined.