N^α-(tert-butoxycarbonyl)-N^β-<1-amino-3-(4-azido-6-carbethoxy-5-methylpyrimidin-2-yl)propion-3-yl>-(S)-β-aminoalanineamide | 129812-66-4

• 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: N^α-(tert-butoxycarbonyl)-N^β-<1-amino-3-(4-azido-6-carbethoxy-5-methylpyrimidin-2-yl)propion-3-yl>-(S)-β-aminoalanineamide
• 英文别名: ethyl 2-[(1R)-3-amino-1-[[(2S)-3-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]amino]-3-oxopropyl]-6-azido-5-methylpyrimidine-4-carboxylate
• CAS: 129812-66-4
• 化学式: C₁₉H₂₉N₉O₆
• 分子量: 479.496
• InChiKey: VWGKUKJCHIHLSB-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.79
• 重原子数：
  34.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  237.38
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  N^α-(tert-butoxycarbonyl)-N^β-<1-amino-3-(4-azido-6-carbethoxy-5-methylpyrimidin-2-yl)propion-3-yl>-(S)-β-aminoalanineamide 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以91%的产率得到N^α-((tert-butyloxy)carbonyl)-N^β-<1-amino-3(R)-(6-amino-4-(ethoxycarbonyl)-5-methylpyrimidin-2-yl)propion-3-yl>-(S)-β-aminoalanine amide
  参考文献：
  名称：

  Synthesis of pyrimidoblamic acid and epipyrimidoblamic acid

  摘要：

  The N-protected pyrimidine moieties of bleomycin (pyrimidoblamic acid, 1) and epibleomycin are reported. In addition to a complete description of a synthetic route outlined earlier (Arai, H.; Hagmann, W. K.; Suguna, H.; Hecht, S. M. J. Am. Chem. Soc 1980, 102,6631), a new route is also presented that provides access to multigram qauantities of pyrimidoblamic acid. Because bleomycin and epibleomycin, which differ only in the orientation of the propionamide substituent, differ significantly in their Cu(II) chelation and DNA cleavage properties, we also prepared an analogue of pyrimidoblamic acid lacking the proprionamide moiety.

  DOI：

  10.1021/jo00313a016
• 作为产物：
  描述：

  3-(4-azido-6-carbethoxy-5-methylpyrimidin-2-yl)-3-bromopropionamide 、 Boc-Dap(NH₂)-CONH₂ 在 碳酸氢钠 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 24.0h， 以48%的产率得到N^α-(tert-butoxycarbonyl)-N^β-<1-amino-3-(4-azido-6-carbethoxy-5-methylpyrimidin-2-yl)propion-3-yl>-(S)-β-aminoalanineamide
  参考文献：
  名称：

  Synthesis of pyrimidoblamic acid and epipyrimidoblamic acid

  摘要：

  The N-protected pyrimidine moieties of bleomycin (pyrimidoblamic acid, 1) and epibleomycin are reported. In addition to a complete description of a synthetic route outlined earlier (Arai, H.; Hagmann, W. K.; Suguna, H.; Hecht, S. M. J. Am. Chem. Soc 1980, 102,6631), a new route is also presented that provides access to multigram qauantities of pyrimidoblamic acid. Because bleomycin and epibleomycin, which differ only in the orientation of the propionamide substituent, differ significantly in their Cu(II) chelation and DNA cleavage properties, we also prepared an analogue of pyrimidoblamic acid lacking the proprionamide moiety.

  DOI：

  10.1021/jo00313a016

文献信息

• AOYAGI, YOSHIAKI;CHORGHADE, MUKUND S.;PADMAPRIYA, ABEYSINGLE A.;SUGUNA, H+, J. ORG. CHEM., 55,(1990) N6, C. 6291-6298
  作者：AOYAGI, YOSHIAKI、CHORGHADE, MUKUND S.、PADMAPRIYA, ABEYSINGLE A.、SUGUNA, H+

  DOI：——

  日期：——