(4R,5R) methyl 4-acetoxy-5-[(tert-butyldimethylsilyl)oxy]-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-2-[N-(methoxycarbonyl)imino]pentanoate | 200055-61-4

• 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: (4R,5R) methyl 4-acetoxy-5-[(tert-butyldimethylsilyl)oxy]-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-2-[N-(methoxycarbonyl)imino]pentanoate
• CAS: 200055-61-4
• 化学式: C₂₆H₃₇BrN₂O₉Si
• 分子量: 629.577
• InChiKey: JRODDLZCXDFBKE-ZHDUNJGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  129.8
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  CbzNH(-2d)[TBDMS(-3)]a-Glc1Me4Ac6I 在 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 二甲基硫 、 乙醇 、 potassium tert-butylate 、 臭氧 、 三苯基膦 、 锌 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 13.0h， 生成 (4R,5R) methyl 4-acetoxy-5-[(tert-butyldimethylsilyl)oxy]-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-2-[N-(methoxycarbonyl)imino]pentanoate
  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

文献信息

• The development of strategies for construction of the aziridine core of the antitumor agents azinomycins A and B
  作者：Robert S. Coleman、Andrew J. Carpenter

  DOI：10.1016/s0040-4020(97)01017-x

  日期：1997.12

  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.