(S,2Z,4E)-ethyl 5-(2-(4-(benzyloxy)phenyl)-1-((tert-butoxycarbonylamino)ethyl)thiazol-4-yl)-2,4-dimethylpenta-2,4-dienoate | 932406-30-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S,2Z,4E)-ethyl 5-(2-(4-(benzyloxy)phenyl)-1-((tert-butoxycarbonylamino)ethyl)thiazol-4-yl)-2,4-dimethylpenta-2,4-dienoate
• 英文别名: (S,2Z,4E)-ethyl 5-(2-(2-(4-(benzyloxy)phenyl)-1-(tert-butoxy-carbonylamino)ethyl)thiazol-4-yl)-2,4-dimethylpenta-2,4-dienoate；ethyl (2Z,4E)-2,4-dimethyl-5-[2-[(1S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(4-phenylmethoxyphenyl)ethyl]-1,3-thiazol-4-yl]penta-2,4-dienoate
• CAS: 932406-30-9
• 化学式: C₃₂H₃₈N₂O₅S
• 分子量: 562.73
• InChiKey: UHSNKWORQCZTBV-FGWLLPCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S,2Z,4E)-ethyl 5-(2-(4-(benzyloxy)phenyl)-1-((tert-butoxycarbonylamino)ethyl)thiazol-4-yl)-2,4-dimethylpenta-2,4-dienoate 在 三氟乙酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 以103 mg的产率得到ethyl (2Z,4E)-5-[2-[(1S)-1-amino-2-(4-phenylmethoxyphenyl)ethyl]-1,3-thiazol-4-yl]-2,4-dimethylpenta-2,4-dienoate
  参考文献：
  名称：

  Preparation and biological evaluation of key fragments and open analogs of scleritodermin A

  摘要：

  The synthesis of key fragments of scleritodermin A. their assembly, and their biological evaluation as cytotoxic and anthelmintic were performed. Highlights of the synthetic route include formation of the alpha-ketoamide linkage and use of stereocontrolled reactions. Open analogs of this natural product were obtained using a convergent strategy. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.040
• 作为产物：
  描述：

  (S,E)-tert-butyl 2-(4-(benzyloxy)phenyl)-1-(4-(2-methyl-3-oxo-prop-1-enyl)thiazol-2-yl)ethylcarbamate 、 2-[二(2,2,2-三氟乙氧基)磷酰]丙酸乙酯 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.5h， 以80%的产率得到(S,2Z,4E)-ethyl 5-(2-(4-(benzyloxy)phenyl)-1-((tert-butoxycarbonylamino)ethyl)thiazol-4-yl)-2,4-dimethylpenta-2,4-dienoate
  参考文献：
  名称：

  巩膜皮蛋白A最初提出和修订的结构的全合成。

  摘要：

  通过使用α-叠氮基羧基基团作为关键的α-酮酰胺前体，实现了最初建议的和修订的巩膜皮蛋白A及其异构体结构的第一次全合成，从而导致了最初结构的修订提议用于天然巩膜硬化蛋白A。

  DOI：

  10.1021/ol801419m

文献信息

• Total Synthesis of the Originally Proposed and Revised Structures of Scleritodermin A
  作者：Sheng Liu、Yong-Mei Cui、Fa-Jun Nan

  DOI：10.1021/ol801419m

  日期：2008.9.1

  The first total synthesis of the originally proposed and revised structure of scleritodermin A, along with an isomer, were achieved by the use of an alpha-azido carboxyl group serving as the key alpha-ketoamide precursor, thus leading to a revision of the structure originally proposed for natural scleritodermin A.

  通过使用α-叠氮基羧基基团作为关键的α-酮酰胺前体，实现了最初建议的和修订的巩膜皮蛋白A及其异构体结构的第一次全合成，从而导致了最初结构的修订提议用于天然巩膜硬化蛋白A。
• Preparation and biological evaluation of key fragments and open analogs of scleritodermin A
  作者：Diver Sellanes、Francisco Campot、Ivana Núñez、Gerardo Lin、Pablo Espósito、Sylvia Dematteis、Jenny Saldaña、Laura Domínguez、Eduardo Manta、Gloria Serra

  DOI：10.1016/j.tet.2010.05.040

  日期：2010.7

  The synthesis of key fragments of scleritodermin A. their assembly, and their biological evaluation as cytotoxic and anthelmintic were performed. Highlights of the synthetic route include formation of the alpha-ketoamide linkage and use of stereocontrolled reactions. Open analogs of this natural product were obtained using a convergent strategy. (C) 2010 Elsevier Ltd. All rights reserved.