Cbz-Arg(Boc)2-OH | 83585-01-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Cbz-Arg(Boc)2-OH
• 英文别名: Cbz-Arg(N,N-diBoc)-OH；Z-Arg(Boc)2-OH；(2S)-5-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-2-(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 83585-01-7
• 化学式: C₂₄H₃₆N₄O₈
• 分子量: 508.572
• InChiKey: CLWOXZHZADAQEW-KRWDZBQOSA-N

物化性质

• 熔点：
  99-101 °C(Solv: 1,4-dioxane (123-91-1))
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  165
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Cbz-Arg(Boc)2-OH 在 N-羟基-7-氮杂苯并三氮唑 、 palladium on carbon 、 氢气 、 三乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.5h， 生成
  参考文献：
  名称：

  丙型肝炎病毒内部核糖体进入位点合成 RNA 结合剂的模块化方法

  摘要：

  DAPper 配体：3,5-二氨基哌啶(DAP) 杂环已被开发为 2-DOS 支架的 RNA 识别药效团的结构模拟物。在这里，我们描述了新型模块化 DAP 配体的合成，这些配体与丙型肝炎病毒内部核糖体进入位点 RNA 中的构象靶标结合。

  DOI：

  10.1002/cbic.201000177
• 作为产物：
  描述：

  Cbz-L-鸟氨酸 、 N,N'-bis-Boc-S-methyl-isothiourea 在 苄基三甲基氢氧化铵 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 40.0h， 生成 Cbz-Arg(Boc)2-OH
  参考文献：
  名称：

  Fmoc-Argω ，ω'（Boc）2 -OH和Z-Argω ，ω'（Boc）2 -OH（肽合成的新精氨酸衍生物）的简便制备方法。

  摘要：

  从Z-Orn-OH和N，N'开始可以轻松地以高收率制备新的精氨酸衍生物Fmoc-Argω ，ω'（Boc）2 -OH和Z- Argω ，ω'（Boc）2 -OH -双（叔丁氧基羰基）-S-甲基异硫脲。

  DOI：

  10.1016/s0040-4039(00)79037-x

文献信息

• [EN] ANTIVIRAL COMPOUNDS FOR THE TREATMENT OF HCV INFECTION<br/>[FR] COMPOSÉS ANTIVIRAUX DESTINÉS AU TRAITEMENT DE L'INFECTION PAR LE VHC
  申请人：UNIV CALIFORNIA

  公开号：WO2009099897A1

  公开（公告）日：2009-08-13

  Disclosed are compounds and methods of synthesis of Formula I for the development of antiviral drugs for the treatment of HCV infection.

  揭示了用于开发治疗HCV感染的抗病毒药物的化合物和合成方法的公式I。
• A Cyclooligomerisation Approach to Backbone-Modified Cyclic Peptides Bearing Guanidinium Arms
  作者：Katrina Jolliffe、Richard Black、Victoria Dungan、Rebecca Li、Philip Young

  DOI：10.1055/s-0029-1219155

  日期：2010.3

  Cyclooligomerisation of the pentafluorophenyl ester derivatives of oxazoles, derived from dipeptides containing protected ornithine, diaminobutanoic acid and diaminopropionic acid residues, gives the cyclic trimers as the major products. Deprotection and treatment with guanidinylating agents provides efficient access to backbone rigidified cyclic peptides with guanidinium functionalised side chains.

  从含有保护的鸟氨酸、二氨基丁酸和二氨基丙酸残基的二肽衍生的噁唑的五氟苯酯衍生物经环二聚化后，主要生成环三聚体。通过脱保护并使用胍基化试剂处理，可高效获得具有胍功能化侧链的骨架刚性化环肽。
• The effect of N-methylation on transition state mimetic inhibitors of the <i>Plasmodium</i> protease, plasmepsin V
  作者：Michelle Gazdik、Matthew T. O'Neill、Sash Lopaticki、Kym N. Lowes、Brian J. Smith、Alan F. Cowman、Justin A. Boddey、Brad E. Sleebs

  DOI：10.1039/c4md00409d

  日期：——

  An N-methylation strategy has been applied to transition state mimetics that are potent inhibitors of plasmepsin V to improve their physical characteristics and their ability to reduce the viability of Plasmodium parasites in culture.

  一种N-甲基化策略已应用于类似过渡态的模拟物，这些模拟物是强效的plasmepsin V抑制剂，以改善它们的物理特性和减少Plasmodium寄生虫在培养中的存活能力。
• Flexible and Convergent Total Synthesis of Cyclotheonamide B
  作者：Harold M. M. Bastiaans、Juul L. van der Baan、Harry C. J. Ottenheijm

  DOI：10.1021/jo961447m

  日期：1997.6.13

  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.
• Total Synthesis of Cyclotheonamide B, a Facile Route towards Analogues
  作者：H Bastiaans

  DOI：10.1016/00404-0399(50)11539-

  日期：1995.8.14

  A flexible, convergent synthesis of Cyclotheonamide B (1b) was developed, starting from the constituent amino acids, using conventional benzyl-, t-butyl- and allyl-based protecting groups. By modification of the key intermediates, this approach allows the preparation of cyclotheonamide analogues.