(2Z,4R,5R) methyl 4-acetoxy-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate | 144001-87-6

• 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]-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate
• 英文别名: benzyl (2S)-2-[(Z,1R,2R)-2-acetyloxy-1-[tert-butyl(dimethyl)silyl]oxy-5-methoxy-4-(methoxycarbonylamino)-5-oxopent-3-enyl]aziridine-1-carboxylate
• CAS: 144001-87-6
• 化学式: C₂₆H₃₈N₂O₉Si
• 分子量: 550.681
• InChiKey: DJGBDASUZKRVDA-KTGGYQKRSA-N

物化性质

• 沸点：
  600.3±55.0 °C(predicted)
• 密度：
  1.185±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  38
• 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]-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以83%的产率得到(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：

  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：

  2-氨基-2-脱氧葡萄糖盐酸盐 在 吡啶 、 2,6-二甲基吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 ammonium cerium(IV) nitrate 、 二甲基硫 、 乙醇 、 camphor-10-sulfonic acid 、 potassium tert-butylate 、 碘 、 碳酸氢钠 、 臭氧 、 三苯基膦 、 锌 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 38.0h， 生成 (2Z,4R,5R) methyl 4-acetoxy-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-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

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.
• 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.