(4S,11S,14S,17S)-11-Benzyl-14-((S)-1-hydroxy-ethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaaza-tricyclo[16.2.1.1^5,8]docosa-1(20),5(22),7,18(21)-tetraene-2,9,12,15-tetraone | 851894-95-6

• 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: (4S,11S,14S,17S)-11-Benzyl-14-((S)-1-hydroxy-ethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaaza-tricyclo[16.2.1.1^5,8]docosa-1(20),5(22),7,18(21)-tetraene-2,9,12,15-tetraone
• 英文别名: (4S,11S,14S,17S)-11-benzyl-14-[(1S)-1-hydroxyethyl]-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexazatricyclo[16.2.1.15,8]docosa-1(20),5(22),7,18(21)-tetraene-2,9,12,15-tetrone
• CAS: 851894-95-6
• 化学式: C₂₅H₂₈N₆O₅S₂
• 分子量: 556.667
• InChiKey: ARCFFCLBNNIVPM-JCEDBOLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  38
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  219
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (4S,11S,14S,17S)-11-Benzyl-14-((S)-1-hydroxy-ethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaaza-tricyclo[16.2.1.1^5,8]docosa-1(20),5(22),7,18(21)-tetraene-2,9,12,15-tetraone 在 伯吉斯试剂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以56%的产率得到didmolamide A
  参考文献：
  名称：

  Total synthesis of didmolamides A and B

  摘要：

  The first total synthesis of didmolamides A (1) and B (2) has been accomplished by the solid phase assembly of thiazole-containing amino acids and commercially available Fmoc-protected amino acids. The synthesis of didmolamide B was also achieved in high yield using solution phase peptide synthesis. The thiazole-containing amino acid composing 1 and 2 was synthesized by a MnO2 oxidation of a thiazoline, prepared from an Ala-Cys dipeptide using bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate. The final macrolactamization was accomplished efficiently by PyBOP and DMAP in solution. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.097
• 作为产物：
  描述：

  Fmoc-Ala-Cys(Trt)-OAllyl 在 4-二甲氨基吡啶 、 manganese(IV) oxide 、 palladium diacetate 、 三氟甲磺酸酐 、 styrene polymer-PPh₃ 、 苯硅烷 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三苯基氧化膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.25h， 生成 (4S,11S,14S,17S)-11-Benzyl-14-((S)-1-hydroxy-ethyl)-4,17-dimethyl-6,19-dithia-3,10,13,16,21,22-hexaaza-tricyclo[16.2.1.1^5,8]docosa-1(20),5(22),7,18(21)-tetraene-2,9,12,15-tetraone
  参考文献：
  名称：

  Total synthesis of didmolamides A and B

  摘要：

  The first total synthesis of didmolamides A (1) and B (2) has been accomplished by the solid phase assembly of thiazole-containing amino acids and commercially available Fmoc-protected amino acids. The synthesis of didmolamide B was also achieved in high yield using solution phase peptide synthesis. The thiazole-containing amino acid composing 1 and 2 was synthesized by a MnO2 oxidation of a thiazoline, prepared from an Ala-Cys dipeptide using bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate. The final macrolactamization was accomplished efficiently by PyBOP and DMAP in solution. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.097

文献信息

• Total synthesis of didmolamides A and B
  作者：Shu-Li You、Jeffery W. Kelly

  DOI：10.1016/j.tetlet.2005.02.097

  日期：2005.4

  The first total synthesis of didmolamides A (1) and B (2) has been accomplished by the solid phase assembly of thiazole-containing amino acids and commercially available Fmoc-protected amino acids. The synthesis of didmolamide B was also achieved in high yield using solution phase peptide synthesis. The thiazole-containing amino acid composing 1 and 2 was synthesized by a MnO2 oxidation of a thiazoline, prepared from an Ala-Cys dipeptide using bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate. The final macrolactamization was accomplished efficiently by PyBOP and DMAP in solution. (c) 2005 Elsevier Ltd. All rights reserved.