methyl (tert-butoxycarbonyl)-L-valyl-D-phenylalaninate | 957753-07-0

• 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: methyl (tert-butoxycarbonyl)-L-valyl-D-phenylalaninate
• 英文别名: Boc-Val-D-Phe-OMe；methyl (2R)-2-[[(2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]-3-phenylpropanoate
• CAS: 957753-07-0
• 化学式: C₂₀H₃₀N₂O₅
• 分子量: 378.469
• InChiKey: VVTQXNCFAHBZEU-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (tert-butoxycarbonyl)-L-valyl-D-phenylalaninate 在 苯甲醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (2R)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-phenylpropanoate
  参考文献：
  名称：

  Comprehensive Study of Sansalvamide A Derivatives and their Structure–Activity Relationships against Drug-Resistant Colon Cancer Cell Lines

  摘要：

  We report an extensive structure-activity relationship (SAR) of 62 compounds active against two drug-resistant colon cancer cell lines. Our comprehensive evaluation of two generations of compounds utilizes SAR, NMR, and molecular modeling to evaluate the key 3D features of potent compounds. Of the seven most potent compounds reported here, five are second-generation, emphasizing our ability to incorporate potent features found in the first generation and utilize their structures to design potency into the second generation. These analogs share no structural homology to current colon cancer drugs, are cytotoxic at levels on par with existing drugs treating other cancers, and demonstrate selectivity for drug-resistant colon cancer cell lines over noncancerous cell lines. Thus, we have established sansalvamide A as an excellent lead for treating, multiple drug-resistant colon cancers.

  DOI：

  10.1021/jm070731a
• 作为产物：
  描述：

  D-苯丙氨酸甲酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 methyl (tert-butoxycarbonyl)-L-valyl-D-phenylalaninate
  参考文献：
  名称：

  从硫代酸和二硫代氨基甲酸酯末端胺构建酰胺和肽的无痕方法†

  摘要：

  已经设计出一种新颖且无痕的策略，其允许将硫代酸和二硫代氨基甲酸酯末端的胺偶联。在较早的天然化学连接方法中，已假定该策略取决于半胱氨酸侧链功能等同物的附着。这种方法能够无痕地去除CS 2以直接生成所需的酰胺键，并且与一系列未保护的氨基酸侧链兼容。通过无痕去除助剂产生酰胺或肽的能力是该方法的重要优点。同时，实现了这种新的肽键形成反应在具有各种结合力的新型内啡肽（EM）衍生物的合成中的应用。

  DOI：

  10.1039/c2sc21317f

文献信息

• Epimerization-Free Block Synthesis of Peptides from Thioacids and Amines with the Sanger and Mukaiyama Reagents
  作者：David Crich、Indrajeet Sharma

  DOI：10.1002/anie.200805782

  日期：2009.3.16

  reaction of C‐terminal thioacids derived from protected amino acids and peptides with the Sanger reagent and other electron‐deficient aryl halides in the presence of a free amine immediately form a peptide bond with the amine. This essentially epimerization‐free method was used for the 4+4 block synthesis of a hindered octapeptide (see scheme; Boc, Pbf, and Trt are protecting groups).

  在游离胺存在下，由受保护氨基酸和肽衍生的C末端硫代酸与Sanger试剂和其他电子不足的芳基卤化物快速反应而形成的高活化硫酯立即与胺形成肽键。该基本无差向异构的方法用于受阻八肽的4 + 4嵌段合成（请参阅方案； Boc，Pbf和Trt是保护基）。
• A rapid and efficient one-pot method for the reduction of N-protected α-amino acids to chiral α-amino aldehydes using CDI/DIBAL-H
  作者：Jakov Ivkovic、Christian Lembacher-Fadum、Rolf Breinbauer

  DOI：10.1039/c5ob01838b

  日期：——

  N-Protected α-amino acids can be easily converted directly into chiral α-amino aldehydes in a one-pot procedure by activation with CDI followed by reduction with DIBAL-H.

  N-保护的α-氨基酸可以通过使用CDI激活后再用DIBAL-H还原，在一个步骤中轻松直接转化为手性α-氨基醛。
• P(RNCH₂CH₂)₃N:  Efficient Catalysts for Transesterifications, Acylations, and Deacylations
  作者：Palanichamy Ilankumaran、J. G. Verkade

  DOI：10.1021/jo981819m

  日期：1999.4.1

  Extremely strong nonionic superbases of the type P(RNCH(2)CH(2))(3)N catalyze the transesterification of carboxylic acid esters with high selectivity and yields at 25 degrees C. These bases also catalyze the deacetylation of alcohols under mild conditions in quantitative yields. Using enol acetates as acylating agents, primary and secondary alcohols are efficiently protected as acetates through the

  P（RNCH（2）CH（2））（3）N类型的极强非离子超强碱催化羧酸酯的酯交换反应具有很高的选择性，并在25°C时产率较高。这些碱还催化在温和条件下醇的脱乙酰以定量的产量。使用烯醇乙酸酯作为酰化剂，伯和仲醇通过这些催化剂的作用被有效地保护为乙酸酯。在反应条件下可以耐受诸如环氧化物，氨基甲酸酯，乙缩醛，恶唑啉，硝基和炔基官能团的取代基。N保护的肽无需明显消旋就可以进行干净的酯交换反应，这使得该方法可能非常有用。
• Backbone-enabled modification of peptides with benzoquinone <i>via</i> palladium-catalyzed δ-C(sp²)–H functionalization
  作者：Fengjie Lu、Yi Sun、Ya-ning Liu、Yujie Geng、Ensheng Zhang、Jian Tang

  DOI：10.1039/d3cc06020a

  日期：——

  Backbone-enabled site-selective modification of peptides with benzoquinone via Pd-catalyzed δ-C(sp2)–H functionalization has been achieved. The amide groups of peptides serve as internal directional groups, facilitating C–H functionalization through a kinetically less favored six-membered palladacycle. This methodology presents novel opportunities for the late-stage site-selective diversification of

  通过Pd 催化的 δ-C(sp 2 )–H 功能化，已经实现了苯醌对肽的主链位点选择性修饰。肽的酰胺基团作为内部定向基团，通过动力学上不太有利的六元环来促进 C-H 官能化。该方法为肽的后期位点选择性多样化提供了新的机会。
• 10.1021/acs.orglett.4c01540
  作者：Tang, Jian、Lu, Fengjie、Zhang, Xinyi、Gao, Zhenqi、Gong, Shuo、Zhang, Ensheng

  DOI：10.1021/acs.orglett.4c01540

  日期：——

  An efficient and concise strategy for the synthesis of cyclic dipeptides via Pd-catalyzed site-selective δ-C(sp2)–H amination/fluorination and N-to-C cyclization is disclosed. The backbone amides within the dipeptides serves as endogenous directing groups, while the desired products were switched by the C-terminal ester group. This chemistry presents a novel and robust alternative to construct cyclodipeptide

  公开了一种通过 Pd 催化的位点选择性 δ-C(sp 2 )–H 胺化/氟化和 N 至 C 环化合成环状二肽的有效且简洁的策略。二肽内的主链酰胺充当内源性导向基团，而所需产物则通过 C 端酯基团进行转换。这种化学方法为构建环二肽片段提供了一种新颖且可靠的替代方案。