N-Alloc-N-Me-(S)-Val-OH | 553636-70-7

• 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: N-Alloc-N-Me-(S)-Val-OH
• 英文别名: Alloc-NMe-Val-OH；allyloxycarbonyl-NMe-Val-OH；L-Valine, N-methyl-N-[(2-propenyloxy)carbonyl]-；(2S)-3-methyl-2-[methyl(prop-2-enoxycarbonyl)amino]butanoic acid
• CAS: 553636-70-7
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: MGQVBEFEZMYUQR-QMMMGPOBSA-N

物化性质

• 沸点：
  316.1±31.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Alloc-N-Me-(S)-Val-OH 在 Grubbs catalyst first generation 作用下， 以 2,2,2-三氟乙醇 、 甲苯 为溶剂， 反应 36.0h， 生成 (4S,7S,14E)-6-[(1S)-1-(3-methoxyphenyl)ethyl]-3-methyl-4,7-di(propan-2-yl)-1,12-dioxa-3,6,9-triazacyclohexadec-14-ene-2,5,8,11-tetrone
  参考文献：
  名称：

  Via Ugi reactions to conformationally fixed cyclic peptidesDedicated to Professor Dr D. Seebach on the occasion of his 65th birthday.

  摘要：

  我们发现了一种简单的方法，即通过多组分反应，然后以容易获得的前体为原料进行闭环反应，制备出含有 N-烷基化氨基酸的几种环肽拟合物。这种组合技术的优点是可以在循环的任何位置添加不同的极性、亲水性或疏水性分子，还可以添加非天然氨基酸。

  DOI：

  10.1039/b210952b
• 作为产物：
  描述：

  Boc-N-甲基-L-缬氨酸 、 氯甲酸烯丙酯 在 三氟乙酸 作用下， 以 1,3-二噁烷 、 二氯甲烷 为溶剂， 以60%的产率得到N-Alloc-N-Me-(S)-Val-OH
  参考文献：
  名称：

  通过构象限制的迁移性进行保护：Triostin A的第一个固相合成。

  摘要：

  DOI：

  10.1002/chem.200800372

文献信息

• Via Ugi reactions to conformationally fixed cyclic peptidesDedicated to Professor Dr D. Seebach on the occasion of his 65th birthday.
  作者：Christina Hebach、Uli Kazmaier

  DOI：10.1039/b210952b

  日期：2003.2.20

  A simple approach to several cyclopeptidmimetics containing an N-alkylated amino acid was found via a multicomponent reaction followed by a ring-closing metathesis starting from readily available precursors. The combinatorial technique has the advantage that different polar, hydrophilic or hydrophobic moieties can be placed at any position in the cycles and unnatural amino acids can also be incorporated.

  我们发现了一种简单的方法，即通过多组分反应，然后以容易获得的前体为原料进行闭环反应，制备出含有 N-烷基化氨基酸的几种环肽拟合物。这种组合技术的优点是可以在循环的任何位置添加不同的极性、亲水性或疏水性分子，还可以添加非天然氨基酸。
• Orthogonal Chemistry for the Synthesis of Thiocoraline–Triostin Hybrids. Exploring their Structure–Activity Relationship
  作者：Judit Tulla-Puche、Sara Auriemma、Chiara Falciani、Fernando Albericio

  DOI：10.1021/jm4006093

  日期：2013.7.11

  The natural compounds triostin and thiocoraline are potent antitumor agents that act as DNA bisintercalators. From a pharmaceutical point of view, these compounds are highly attractive although they present a low pharmacokinetic profile, in part due to their low solubility. Synthetically, they represent a tour de force because no robust strategies have been developed to access a broad range of these bicyclic (depsi)peptides in a straightforward manner. Here we describe solid-phase strategies to synthesize new bisintercalators, such as thiocoraline triostin hybrids, as well is analogues bearing soluble tags. Orthogonal protection schemes (up to, five from: Fmoc, Boc Alloc, pNZ, o-NBS, and Troc), together with the right concourse of the coupling reagents (HOSu, HOBt, HOAt, Oxyma, EDC, DIPCDI, PyAOP, PyBOP, HATU, COMU), were crucial to establish the synthetic plan. In vitro studies and structure activity relationships have been shown trends in the structure activity relationship that Will facilitate the design of new bisintercalators.
• Protection by Conformationally Restricted Mobility: First Solid-Phase Synthesis of Triostin A
  作者：Judit Tulla-Puche、Eleonora Marcucci、Manuel Fermin、Núria Bayó-Puxan、Fernando Albericio

  DOI：10.1002/chem.200800372

  日期：2008.5.19
• A straightforward approach towards cyclic peptides via ring-closing metathesis—scope and limitations
  作者：Uli Kazmaier、Christina Hebach、Anja Watzke、Sabine Maier、Heike Mues、Volker Huch

  DOI：10.1039/b411228h

  日期：——

  N- and C-terminal diallylated peptides are obtained by several approaches, such as peptide Claisen rearrangement, N- and O- allylation, and the Ugi reaction of allyl-protected components. These diallylated peptides are suitable substrates for ring-closing metathesis and the success of this cyclisation was investigated with respect to the ring size, the position of the allyl moieties and the reaction

  N-和C-末端二烯丙基化的肽可通过几种方法获得，例如肽克莱森重排，N-和O-烯丙基化以及烯丙基保护的组分的Ugi反应。这些二烯丙基化的肽是适合于闭环复分解的底物，并且关于环的大小，烯丙基部分的位置和反应参数研究了这种环化的成功。通常，烯丙基甘氨酸亚基和N-烯丙基化酰胺的环化可获得优异的收率，而烯丙基酯和烯丙基氨基甲酸酯则经常出现严重的问题。但是，在最佳条件下可获得高达73％的产率，并且新生成的双键具有极好的反选择性。