methyl (S)-2-(3-(2-(benzyloxycarbonyl)amino-3-phenylpropyl)thioureido)-4-methylpentanoate | 1172596-92-7

• 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: methyl (S)-2-(3-(2-(benzyloxycarbonyl)amino-3-phenylpropyl)thioureido)-4-methylpentanoate
• 英文别名: Z-Phe-ψ[CH2NHCSNH]-Leu-OMe；methyl (2S)-4-methyl-2-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propyl]carbamothioylamino]pentanoate
• CAS: 1172596-92-7
• 化学式: C₂₅H₃₃N₃O₄S
• 分子量: 471.621
• InChiKey: BHOWZYOXMGPZDQ-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (S)-2-(3-(2-(benzyloxycarbonyl)amino-3-phenylpropyl)thioureido)-4-methylpentanoate 、 sodium cyanamide 在 三乙胺 、 mercury dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以69%的产率得到(S)-methyl 2-((E)-3-((S)-2-(benzyloxycarbonylamino)-3-phenylpropyl)-2-cyanoguanidin-1-yl)-4-methylpentanoate
  参考文献：
  名称：

  Basavaprabhu; Sharanabai, Kupendra M.; Prabhu, Girish, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, # 9, p. 1131 - 1135

  摘要：

  DOI：
• 作为产物：
  描述：

  (2S)-2-氨基-4-甲基戊酸甲酯 、 Cbz-Phe-ψ[CH₂NCS] 在 N,N-二异丙基乙胺 作用下， 以72%的产率得到methyl (S)-2-(3-(2-(benzyloxycarbonyl)amino-3-phenylpropyl)thioureido)-4-methylpentanoate
  参考文献：
  名称：

  N-Urethane-Protected Amino Alkyl Isothiocyanates: Synthesis, Isolation, Characterization, and Application to the Synthesis of Thioureidopeptides

  摘要：

  Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z' = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P2(1)2(1)2(1).

  DOI：

  10.1021/jo900675s

文献信息

• <i>N</i>-Urethane-Protected Amino Alkyl Isothiocyanates: Synthesis, Isolation, Characterization, and Application to the Synthesis of Thioureidopeptides
  作者：Vommina V. Sureshbabu、Shankar A. Naik、H. P. Hemantha、N. Narendra、Ushati Das、Tayur N. Guru Row

  DOI：10.1021/jo900675s

  日期：2009.8.7

  Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z' = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P2(1)2(1)2(1).
• Basavaprabhu; Sharanabai, Kupendra M.; Prabhu, Girish, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, # 9, p. 1131 - 1135
  作者：Basavaprabhu、Sharanabai, Kupendra M.、Prabhu, Girish、Krishnamurthy、Sureshbabu, Vommina V.

  DOI：——

  日期：——