methyl (2E)-2-[(3R,4R,5S)-3-acetyloxy-4-[tert-butyl(dimethyl)silyl]oxy-1-azabicyclo[3.1.0]hexan-2-ylidene]-2-(methoxycarbonylamino)acetate | 144017-85-6

• 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: methyl (2E)-2-[(3R,4R,5S)-3-acetyloxy-4-[tert-butyl(dimethyl)silyl]oxy-1-azabicyclo[3.1.0]hexan-2-ylidene]-2-(methoxycarbonylamino)acetate
• CAS: 144017-85-6
• 化学式: C₁₈H₃₀N₂O₇Si
• 分子量: 414.531
• InChiKey: KTUJHDGDDUVYOF-BJRYOKNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 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 、 三乙基硅烷 、 potassium tert-butylate 、 三乙胺 、 palladium dichloride 作用下， 以 四氢呋喃 为溶剂， 生成 methyl (2E)-2-[(3R,4R,5S)-3-acetyloxy-4-[tert-butyl(dimethyl)silyl]oxy-1-azabicyclo[3.1.0]hexan-2-ylidene]-2-(methoxycarbonylamino)acetate
  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

文献信息

• Synthesis of the aziridino[1,2-a]pyrrolidine substructure of the antitumor agents azinomycin A and B
  作者：Robert S. Coleman、Andrew J. Carpenter

  DOI：10.1021/jo00048a006

  日期：1992.10

  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.