methyl (S)-2-(3-(2-(((9H-fluoren-9-yl)methoxy)carbonyl)aminoethyl)thioureido)-3-phenylpropanoate | 1172596-85-8

• 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-(((9H-fluoren-9-yl)methoxy)carbonyl)aminoethyl)thioureido)-3-phenylpropanoate
• 英文别名: Fmoc-Gly-ψ[CH2NHCSNH]-Phe-OMe；methyl (2S)-2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethylcarbamothioylamino]-3-phenylpropanoate
• CAS: 1172596-85-8
• 化学式: C₂₈H₂₉N₃O₄S
• 分子量: 503.622
• InChiKey: SIVTXHGOEWRGSU-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 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-(((9H-fluoren-9-yl)methoxy)carbonyl)aminoethyl)thioureido)-3-phenylpropanoate 、 3-甲基苯胺 在 三乙胺 、 mercury dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以66%的产率得到
  参考文献：
  名称：

  “硫脲肽”：用于合成N，N'，N”-三取代胍肽模拟物的新型合成子

  摘要：

  的合成Ñ α -保护的N，N'，N“适当装饰肽骨架三取代guanidinopeptide模拟物分子已经被划定在采用的HgCl一锅2作为脱硫剂。手性Ñ α -保护的酯thioureidopeptide被用作合成子为标题分子的合成。该方案是简单的，并且所采用的反应条件温和，适合于氨基酸化学。

  DOI：

  10.1007/s10989-015-9496-2
• 作为产物：
  描述：

  (9H-fluoren-9-yl)methyl 2-isothiocyanatoethylcarbamate 、 L-苯丙氨酸甲酯盐酸盐 在 锌 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到methyl (S)-2-(3-(2-(((9H-fluoren-9-yl)methoxy)carbonyl)aminoethyl)thioureido)-3-phenylpropanoate
  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).
• “Thioureidopeptide”: Novel Synthon for the Synthesis of N, N′, N″-Trisubstituted Guanidinopeptide Mimics
  作者：Hosamani Basavaprabhu、Girish Prabhu、M. Krishnamurthy、P. Nageswara Rao、Vommina V. Sureshbabu

  DOI：10.1007/s10989-015-9496-2

  日期：2016.6

  The synthesis of N α-protected N,N′,N″-trisubstituted guanidinopeptide mimic molecules suitably decorated in peptide backbone has been delineated in one pot employing HgCl2 as a desulphurizing agent. Chiral N α-protected thioureidopeptide esters were employed as synthons for the synthesis of title molecules. The protocol is simple and the reaction conditions employed were mild, amenable to the amino

  的合成Ñ α -保护的N，N'，N“适当装饰肽骨架三取代guanidinopeptide模拟物分子已经被划定在采用的HgCl一锅2作为脱硫剂。手性Ñ α -保护的酯thioureidopeptide被用作合成子为标题分子的合成。该方案是简单的，并且所采用的反应条件温和，适合于氨基酸化学。