Boc-Trp(Cbz)-OMe | 86961-51-5

• 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-Trp(Cbz)-OMe
• 英文别名: benzyl (S)-3-(2-((tert-butoxycarbonyl)amino)-3-methoxy-3-oxopropyl)-1H-indole-1-carboxylate；N^α-Boc-N-Cbz-L-tryptophan methyl ester；(S)-benzyl 3-(2-((tert-butoxycarbonyl)amino)-3-methoxy-3-oxopropyl)-1H-indole-1-carboxylate；benzyl 3-[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]indole-1-carboxylate
• CAS: 86961-51-5
• 化学式: C₂₅H₂₈N₂O₆
• 分子量: 452.507
• InChiKey: OGLWOKHXIRIDTD-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  95.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Trp(Cbz)-OMe 在 三氟乙酸 作用下， 反应 4.0h， 生成 N-benzyloxycarbonyl tryptophan methyl ester
  参考文献：
  名称：

  AgNTf2-Mediated Arylation of Bromopyrroloindolines

  摘要：

  The silver(I)-mediated arylation of bromopyrroloindolines was developed. The selection of silver salts was crucial to obtain arylated compounds in high yields. Among the various tested silver(I) salts, AgNTf2 was the most effective agent for arylation. Reactions using various electron-rich aromatic compounds revealed that the developed conditions are suitable for the arylation of a broad range of aromatic compounds, including benzene derivatives, furan, thiophene, and pyrrole.

  DOI：

  10.3987/com-17-13777
• 作为产物：
  描述：

  苄氧甲酸酐 、 N-[叔丁氧羰基]-L-色氨酸甲酯 在 4-二甲氨基吡啶 作用下， 生成 Boc-Trp(Cbz)-OMe
  参考文献：
  名称：

  Deprotection of heteroaromatic carbamates via a base-catalyzed methanolysis

  摘要：

  A simple and mild method for the deprotection of heteroaromatic carbamates via methanolysis using a catalytic amount of base such as sodium methoxide, DBU, or Verkade's base (proazaphosphatranes) is presented. Carbantate protecting group of an aliphatic amine is not affected under these conditions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.028

文献信息

• Chemoselective N-Acylation of Indoles and Oxazolidinones with Carbonylazoles
  作者：Stephen T. Heller、Erica E. Schultz、Richmond Sarpong

  DOI：10.1002/anie.201203976

  日期：2012.8.13

  Unique reactivity: In the presence of more reactive amine and alcohol functional groups and of carboxylic acids, the chemoselective N‐acylation of indoles (see scheme) and oxazolidinones is achieved by taking advantage of the unique reactivity of carbonylazole acylating agents with catalytic amounts of 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU).

  独特的反应性：在存在更多的反应性胺和醇官能团以及羧酸的情况下，吲哚和恶唑烷酮的化学选择性N-酰化是通过利用催化量为1的羰基唑酰化剂的独特反应性来实现的，8-二氮杂双环[5.4.0]十一月-7-烯（DBU）。
• Selenium–Iodine Cooperative Catalyst for Chlorocyclization of Tryptamine Derivatives
  作者：Takahiro Horibe、Shuhei Ohmura、Kazuaki Ishihara

  DOI：10.1021/acs.orglett.7b02613

  日期：2017.10.20

  Chlorocyclization of tryptamine derivatives has been developed with the use of a diphenyl diselenide–iodine cooperative catalyst. Various tryptamine derivatives can be smoothly converted to the corresponding C3a-chlorohexahydropyrrolo[2,3-b]indoles. Additionally, we demonstrate the formal total syntheses of (−)-psychotriasine and (−)-acetylardeemin by introducing nucleophiles to the C3a position of

  使用二苯基二硒化物-碘协同催化剂已经开发了色胺胺衍生物的氯环化反应。各种色胺衍生物可以平稳地转化为相应的C3a-氯六氢吡咯并[2,3- b ]吲哚。此外，我们通过将亲核试剂引入产品的C3a位置，证明了（-）-精神神经碱和（-）-乙酰氨基乙胺的正式总合成。
• Electrochemical synthesis of 3a-bromofuranoindolines and 3a-bromopyrroloindolines mediated by MgBr₂
  作者：Ju Wu、Hussein Abou-Hamdan、Régis Guillot、Cyrille Kouklovsky、Guillaume Vincent

  DOI：10.1039/c9cc09276e

  日期：——

  electrochemical approach to perform the bromo cyclization of tryptophol, tryptamine and tryptophan derivatives. The 3a-bromofuranoindolines and 3a-bromopyrroloindolines obtained are of interest in the total synthesis of natural products. This dearomative procedure relies on the generation of an electrophilic bromine reagent by the electrochemical oxidation of MgBr2. No organic byproducts are generated

  我们报告了一种高效且环保的电化学方法，可对色酚，色胺和色氨酸衍生物进行溴环化。获得的3a-溴呋喃并吲哚啉和3a-溴吡咯并吲哚啉在天然产物的总合成中是令人感兴趣的。该脱芳香步骤依赖于通过MgBr2的电化学氧化产生亲电溴试剂。该方案不会产生有机副产物，从而避免了使用额外的电解质。
• Concise Total Synthesis of (+)-Asperazine, (+)-Pestalazine A, and (+)-<i>iso</i>-Pestalazine A. Structure Revision of (+)-Pestalazine A
  作者：Richard P. Loach、Owen S. Fenton、Mohammad Movassaghi

  DOI：10.1021/jacs.5b12392

  日期：2016.1.27

  The concise, enantioselective total syntheses of (+)-asperazine (1), (+)-iso-pestalazine A (2), and (+)-pestalazine A (3) have been achieved by the development of a late-stage C3-C8' Friedel-Crafts union of polycyclic diketopiperazines. Our modular strategy enables the union of complex polycyclic diketopiperazines in virtually their final forms, thus providing rapid and highly convergent assembly at

  通过开发后期 C3，实现了 (+)-阿哌嗪 (1)、(+)-异-哌司他嗪 A (2) 和 (+)-哌司他嗪 A (3) 的简洁、对映选择性全合成-C8' 多环二酮哌嗪的弗里德-克来福特联合。我们的模块化策略使得复杂的多环二酮哌嗪几乎以最终形式结合，从而在这些二聚生物碱具有挑战性的四元立构中心处提供快速且高度收敛的组装。这种碳-碳键形成的重要性可以通过有效克服的多种限制来衡量，即两个反应位点处的大量空间拥挤、C8'在N1'上对C3碳阳离子的亲核加成以及大量的反应性由在偶联事件中使用复杂的二酮哌嗪片段引起。鉴于在产生的高反应性 C3 碳阳离子存在的情况下观察到的竞争反应途径很少，通过我们的研究进化出的二氢吲哚 π-亲核试剂的成功值得注意。(+)-哌司他嗪 A 的首次全合成也使我们能够修改这种天然生物碱的分子结构。
• AgNTf2-Mediated Arylation of Bromopyrroloindolines
  作者：Hidetoshi Tokuyama、Soichiro Sato、Azusa Hirayama、Tohma Adachi、Daichi Kawauchi、Hirofumi Ueda

  DOI：10.3987/com-17-13777

  日期：——

  The silver(I)-mediated arylation of bromopyrroloindolines was developed. The selection of silver salts was crucial to obtain arylated compounds in high yields. Among the various tested silver(I) salts, AgNTf2 was the most effective agent for arylation. Reactions using various electron-rich aromatic compounds revealed that the developed conditions are suitable for the arylation of a broad range of aromatic compounds, including benzene derivatives, furan, thiophene, and pyrrole.