(S)-methyl 2-(2,3-bis(N-tert-butoxycarbonyl)guanidino)-3-phenylpropanoate

• 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: (S)-methyl 2-(2,3-bis(N-tert-butoxycarbonyl)guanidino)-3-phenylpropanoate
• 英文别名: methyl (S)-2-(N,N'-bis(tert-butoxycarbonyl)guanidino)-3-phenylpropionate；methyl (2S)-2-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-3-phenylpropanoate
• 化学式: C₂₁H₃₁N₃O₆
• 分子量: 421.494
• InChiKey: BAFRDQPLKFLCJO-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-(2,3-bis(N-tert-butoxycarbonyl)guanidino)-3-phenylpropanoate 在 lithium hydroxide 、 水 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以98%的产率得到(2S)-2-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-3-phenylpropanoic acid
  参考文献：
  名称：

  Convergent and Stereospecific Synthesis of Molecules Containing α-Functionalized Guanidiniums via α-Guanidino Acids

  摘要：

  [Graphics]To introduce chirality and functional groups adjacent to guanidiniums to modulate specificity and affinity in recognition, N,N'-bis(Boc)-alpha-guanidino acids were synthesized from alpha-amino acid methyl esters. Protected alpha-guanidino acids coupled to cyclohexylamine and trans- 1,4-diaminocyclohexane in good yield and with retention of stereochemistry. Boc deprotection was conducted under mild acidic conditions (0.5 M HCl/EtOAc) to minimize epimerization. The deprotected guanidinium is configurationally stable under more acidic conditions. This approach represents a practical, convergent, stereospecific methodology to introduce chiral cc-substituted guanidinium groups into molecules.

  DOI：

  10.1021/jo701766c
• 作为产物：
  描述：

  L-苯丙氨酸甲酯 、 N,N′-二-Boc-硫脲 在 碘化1,2-二甲基吡啶鎓 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到(S)-methyl 2-(2,3-bis(N-tert-butoxycarbonyl)guanidino)-3-phenylpropanoate
  参考文献：
  名称：

  Facile and Efficient Guanylation of Amines Using Thioureas and Mukaiyama's Reagent

  摘要：

  DOI：

  10.1021/jo962196k

文献信息

• A Mild and Inexpensive Procedure for the Synthesis of N,N′-Di-Boc-Protected Guanidines
  作者：Andrea Porcheddu、Lidia De Luca、Giampaolo Giacomelli

  DOI：10.1055/s-0029-1218365

  日期：2009.12

  A novel and efficient synthetic procedure for converting a diverse set of amines to N,N′ -di-Boc-protected guanidines is described. The methodology comprises the use of cyanuric chloride (TCT) as activating reagent for di-Boc-thiourea. The employ of inexpensive TCT instead of classical HgCl 2 eliminates the environmental hazard of heavy-metal waste without appreciable loss of yield or reactivity. This

  描述了一种将多种胺转化为 N,N' -di-Boc 保护的胍的新型有效合成程序。该方法包括使用氰尿酰氯 (TCT) 作为二-Boc-硫脲的活化剂。使用廉价的 TCT 代替经典的 HgCl 2 消除了重金属废物对环境的危害，而不会显着降低产量或反应性。该协议为目前使用的胺类鸟苷酸化提供了另一种途径。
• Solid-Phase Synthesis of Peptide Thioureas and Thiazole-Containing Macrocycles through Ru-Catalyzed Ring-Closing Metathesis
  作者：A. Emil Cohrt、Thomas E. Nielsen

  DOI：10.1021/co400102v

  日期：2014.2.10

  N-Terminally modified alpha-thiourea peptides can selectively be synthesized on solid support under mild reaction conditions using N,N'-di-Boc-thiourea and Mukaiyama's reagent (2-chloro-l-methyl-pyridinium iodide). This N-terminal modification applies to the 20 proteinogenic amino acid residues on three commonly used resins for solid-phase synthesis. Complementary methods for the synthesis of alpha-guanidino peptides have also been developed. The thiourea products underwent quantitative reactions with alpha-halo ketones to form thiazoles in excellent purities and yields. When strategically installed between two alkene moieties, said thiazole core was conveniently embedded in peptide macrocycles via Ru-catalyzed ring-closing metathesis reactions. Various 15-17 membered macrocycles were easily accessible in all diastereomeric forms using this methodology. The developed "build/couple/pair" strategy is well suited for the generation of larger and stereochemically complete screening libraries of thiazole-containing peptide macrocycles.