(S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-thiopropionylamino)-3-(4-methoxy-phenyl)-propionylamino]-propionic acid methyl ester | 684233-21-4

• 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)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-thiopropionylamino)-3-(4-methoxy-phenyl)-propionylamino]-propionic acid methyl ester
• 英文别名: Boc-thionoAla-Tyr(Me)-Ala-OMe；methyl (2S)-2-[[(2S)-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanethioyl]amino]propanoyl]amino]propanoate
• CAS: 684233-21-4
• 化学式: C₂₂H₃₃N₃O₆S
• 分子量: 467.587
• InChiKey: OGEYRTPFBRRBFN-ZQIUZPCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  147
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲酰肼 、 (S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-thiopropionylamino)-3-(4-methoxy-phenyl)-propionylamino]-propionic acid methyl ester 在 mercury(II) diacetate 、 4 A molecular sieve 、 对甲苯磺酸 作用下， 以 乙腈 、 氯仿 为溶剂， 反应 10.33h， 以79%的产率得到(S)-2-[(S)-2-[3-((S)-1-tert-Butoxycarbonylamino-ethyl)-[1,2,4]triazol-4-yl]-3-(4-methoxy-phenyl)-propionylamino]-propionic acid methyl ester
  参考文献：
  名称：

  Semisynthesis of an Analogue of Antitumor Bicyclic Hexapeptide RA-VII by Fixing the Ala-2/Tyr-3 Bond to Cis by Incorporating a Triazole cis-Amide Bond Surrogate

  摘要：

  We prepared an analogue of an antitumor bicyclic hexapeptide RA-VII whose amide configuration between residues 2 and 3 was fixed to cis by incorporating a triazole cis-amide bond surrogate. This analogue was shown, by NMR studies, to take almost the same conformation as that of the minor conformer of RA-VII. It showed no cytotoxic activity.

  DOI：

  10.1021/ol040005r
• 作为产物：
  描述：

  Boc-Tyr(OMe)-Ala-OMe 在 盐酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 1.33h， 生成 (S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-thiopropionylamino)-3-(4-methoxy-phenyl)-propionylamino]-propionic acid methyl ester
  参考文献：
  名称：

  Semisynthesis of an Analogue of Antitumor Bicyclic Hexapeptide RA-VII by Fixing the Ala-2/Tyr-3 Bond to Cis by Incorporating a Triazole cis-Amide Bond Surrogate

  摘要：

  We prepared an analogue of an antitumor bicyclic hexapeptide RA-VII whose amide configuration between residues 2 and 3 was fixed to cis by incorporating a triazole cis-amide bond surrogate. This analogue was shown, by NMR studies, to take almost the same conformation as that of the minor conformer of RA-VII. It showed no cytotoxic activity.

  DOI：

  10.1021/ol040005r

文献信息

• Semisynthesis of an Analogue of Antitumor Bicyclic Hexapeptide RA-VII by Fixing the Ala-2/Tyr-3 Bond to <i>Cis</i> by Incorporating a Triazole <i>cis</i>-Amide Bond Surrogate
  作者：Yukio Hitotsuyanagi、Shuichi Motegi、Tomoyo Hasuda、Koichi Takeya

  DOI：10.1021/ol040005r

  日期：2004.4.1

  We prepared an analogue of an antitumor bicyclic hexapeptide RA-VII whose amide configuration between residues 2 and 3 was fixed to cis by incorporating a triazole cis-amide bond surrogate. This analogue was shown, by NMR studies, to take almost the same conformation as that of the minor conformer of RA-VII. It showed no cytotoxic activity.