ethyl 2-[(1R,3R)-3-{[(tert-butoxy)carbonyl]amino}-1-[(tert-butyldimethylsilyl)oxy]-4-methylpentyl]-1,3-thiazole-4-carboxylate | 1303556-55-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-[(1R,3R)-3-{[(tert-butoxy)carbonyl]amino}-1-[(tert-butyldimethylsilyl)oxy]-4-methylpentyl]-1,3-thiazole-4-carboxylate
• 英文别名: ethyl 2-[(1R,3R)-1-[tert-butyl(dimethyl)silyl]oxy-4-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]pentyl]-1,3-thiazole-4-carboxylate
• CAS: 1303556-55-9
• 化学式: C₂₃H₄₂N₂O₅SSi
• 分子量: 486.748
• InChiKey: XWPGVCDWGXAOGC-SJLPKXTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  ethyl 2-[(1R,3R)-3-{[(tert-butoxy)carbonyl]amino}-1-[(tert-butyldimethylsilyl)oxy]-4-methylpentyl]-1,3-thiazole-4-carboxylate 在 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.17h， 生成
  参考文献：
  名称：

  The Multiple Multicomponent Approach to Natural Product Mimics: Tubugis, N-Substituted Anticancer Peptides with Picomolar Activity

  摘要：

  The synthesis of a new generation of highly cytotoxic tubulysin analogues (i.e., tubugis) is described. In the key step, the rare, unstable, and synthetically difficult to introduce tertiary amide-N,O-acetal moiety required for high potency in natural tubulysins is replaced by a dipeptoid element formed in an Ugi four-component reaction. Two of the four components required are themselves produced by other multicomponent reactions (MCRs). Thus, the tubugis represent the first examples of the synthesis of natural-product-inspired compounds using three intertwined isonitrile MCRs.

  DOI：

  10.1021/ja2022027
• 作为产物：
  描述：

  ethyl 2-(3-((tert-butoxycarbonyl)amino)-4-methylpentanoyl)thiazole-4-carboxylate 在 咪唑 、 Noyori's catalyst 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 ethyl 2-[(1R,3R)-3-{[(tert-butoxy)carbonyl]amino}-1-[(tert-butyldimethylsilyl)oxy]-4-methylpentyl]-1,3-thiazole-4-carboxylate
  参考文献：
  名称：

  [EN] TUBULYSINS AND PROTEIN-TUBULYSIN CONJUGATES
  [FR] TUBULYSINES ET CONJUGUÉS TUBULYSINES-PROTÉINES

  摘要：

  公开号：

  WO2021262910A3

文献信息

• The Multiple Multicomponent Approach to Natural Product Mimics: Tubugis, N-Substituted Anticancer Peptides with Picomolar Activity
  作者：Orlando Pando、Sebastian Stark、Annika Denkert、Andrea Porzel、Rainer Preusentanz、Ludger A. Wessjohann

  DOI：10.1021/ja2022027

  日期：2011.5.25

  The synthesis of a new generation of highly cytotoxic tubulysin analogues (i.e., tubugis) is described. In the key step, the rare, unstable, and synthetically difficult to introduce tertiary amide-N,O-acetal moiety required for high potency in natural tubulysins is replaced by a dipeptoid element formed in an Ugi four-component reaction. Two of the four components required are themselves produced by other multicomponent reactions (MCRs). Thus, the tubugis represent the first examples of the synthesis of natural-product-inspired compounds using three intertwined isonitrile MCRs.
• [EN] TUBULYSINS AND PROTEIN-TUBULYSIN CONJUGATES<br/>[FR] TUBULYSINES ET CONJUGUÉS TUBULYSINES-PROTÉINES
  申请人：REGENERON PHARMA

  公开号：WO2021262910A3

  公开（公告）日：2022-04-21