(2Z,4R,5R) methyl 4-acetoxy-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate | 144070-33-7

• 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: (2Z,4R,5R) methyl 4-acetoxy-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate
• 英文别名: benzyl (2S)-2-[(Z,1R,2S)-2-acetyloxy-3-bromo-1-[tert-butyl(dimethyl)silyl]oxy-5-methoxy-4-(methoxycarbonylamino)-5-oxopent-3-enyl]aziridine-1-carboxylate
• CAS: 144070-33-7
• 化学式: C₂₆H₃₇BrN₂O₉Si
• 分子量: 629.577
• InChiKey: UIWJNMCPIXZRMN-LOEFXOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2Z,4R,5R) methyl 4-acetoxy-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate 在 三乙基硅烷 、 三乙胺 、 palladium dichloride 作用下， 反应 2.0h， 以100%的产率得到methyl (E,4S,5R)-4-acetyloxy-5-[(2S)-aziridin-2-yl]-3-bromo-5-[tert-butyl(dimethyl)silyl]oxy-2-(methoxycarbonylamino)pent-2-enoate
  参考文献：
  名称：

  The development of strategies for construction of the aziridine core of the antitumor agents azinomycins A and B

  摘要：

  The synthesis of the C6-C13 aziridino[1,2a]pyrrolidine core substructure of the antitumor agents azinomycins A (1a) and B (1b) is described. Key synthetic steps included Wadsworth-Horner-Emmons olefination for formation of the C7-C8 double bond, an E-selective electrophilic bromination of the C8 position, and a stereospecific intramolecular addition-elimination reaction sequence for formation of the N-C8 pyrrolidine bond. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)01017-x
• 作为产物：
  描述：

  (4R,5R) methyl 4-acetoxy-5-[(tert-butyldimethylsilyl)oxy]-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-2-[N-(methoxycarbonyl)imino]pentanoate 在 三乙烯二胺 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到(2Z,4R,5R) methyl 4-acetoxy-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate
  参考文献：
  名称：

  Synthesis of the aziridino[1,2-a]pyrrolidine substructure of the antitumor agents azinomycin A and B

  摘要：

  A stereoselective synthesis of the central aziridino[1,2-alpha]pyrrolidine substructure (19) of the antitumor agents azinomycin A and B is reported and featured as the key step an intramolecular Michael addition-elimination reaction between the aziridine and beta-bromo acrylate of intermediate 18; this compound was efficiently constructed via aldehyde 14, which was prepared from D-glucosamine.

  DOI：

  10.1021/jo00048a006