ethyl 2(R)-<1-<<2(S)-<((tert-butyloxy)carbonyl)amino>-2-carbamoylethyl>amino>-2-<((4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl)carbonyl>-2(R)-(methylthio)ethyl>-6-amino-5-methylpyrimidine-4-carboxylate | 147975-83-5

• 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: ethyl 2(R)-<1-<<2(S)-<((tert-butyloxy)carbonyl)amino>-2-carbamoylethyl>amino>-2-<((4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl)carbonyl>-2(R)-(methylthio)ethyl>-6-amino-5-methylpyrimidine-4-carboxylate
• 英文别名: ethyl 6-amino-2-[(1R,2R)-1-[[(2S)-3-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]amino]-3-[(4S,5R)-4-methyl-2-oxo-5-phenyl-1,3-oxazolidin-3-yl]-2-methylsulfanyl-3-oxopropyl]-5-methylpyrimidine-4-carboxylate
• CAS: 147975-83-5
• 化学式: C₃₀H₄₁N₇O₈S
• 分子量: 659.764
• InChiKey: UHAWIVDQGLQXJI-XXBFSGCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  244
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  ethyl 2(R)-<1-<<2(S)-<((tert-butyloxy)carbonyl)amino>-2-carbamoylethyl>amino>-2-<((4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl)carbonyl>-2(R)-(methylthio)ethyl>-6-amino-5-methylpyrimidine-4-carboxylate 在 偶氮二异丁腈 、 氨 、 三正丁基氢锡 作用下， 以 乙醇 、 苯 为溶剂， 反应 1.75h， 生成 N^α-((tert-butyloxy)carbonyl)-N^β-<1-amino-3(S)-(6-amino-4-(ethoxycarbonyl)-5-methylpyrimidin-2-yl)propion-3-yl>-(S)-β-aminoalanine amide
  参考文献：
  名称：

  Boger, Dale L.; Menezes, Royce F.; Honda, Takeshi, Angewandte Chemie, 1993, vol. 105, # 2, p. 310 - 311

  摘要：

  DOI：
• 作为产物：
  描述：

  Boc-Dap(NH₂)-CONH₂ 在 4 A molecular sieve 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 18.0h， 生成 ethyl 2(R)-<1-<<2(S)-<((tert-butyloxy)carbonyl)amino>-2-carbamoylethyl>amino>-2-<((4S,5R)-4-methyl-5-phenyl-2-oxazolidinyl)carbonyl>-2(R)-(methylthio)ethyl>-6-amino-5-methylpyrimidine-4-carboxylate
  参考文献：
  名称：

  Boger, Dale L.; Menezes, Royce F.; Honda, Takeshi, Angewandte Chemie, 1993, vol. 105, # 2, p. 310 - 311

  摘要：

  DOI：

文献信息

• Boger, Dale L.; Menezes, Royce F.; Honda, Takeshi, Angewandte Chemie, 1993, vol. 105, # 2, p. 310 - 311
  作者：Boger, Dale L.、Menezes, Royce F.、Honda, Takeshi

  DOI：——

  日期：——
• Total Synthesis of Bleomycin A2 and Related Agents. 2. Synthesis of (-)-Pyrimidoblamic Acid, epi-(+)-Pyrimidoblamic Acid, (+)-Desacetamidopyrimidoblamic Acid, and (-)-Descarboxamidopyrimidoblamic Acid
  作者：Dale L. Boger、Takeshi Honda、Qun Dang

  DOI：10.1021/ja00092a012

  日期：1994.6

  Full details of concise syntheses of (-)-pyrimidoblamic acid (1), the authentic heterocyclic core of the bleomycin A(2) metal binding domain, as well as the key substructure analogs epi-(+)-pyrimidoblamic acid (2), (+)-desacetamidopyrimidoblamic acid (3), and (-)-descarboxamidppyrimidoblamic acid (4) are described. Key to the approach is the implementation of an inverse electron demand [4 + 2] cycloaddition reaction of 2,4,6-tris(ethoxycarbonyl)-1,3,5-triazine with 1-(dibenzylamino)-1-propyne or in situ generated 1,1-diaminopropene for the one-step preparation of an appropriately functionalized pyrimidine nucleus. The development and subsequent implementation of a diastereoselective imine addition reaction of optically active N-acyloxazolidinone enolates provided a stereocontrolled introduction of the pyrimidoblamic acid C2 acetamido side chain. Chemical studies which unambiguously establish and confirm the absolute configuration of the C2 acetamido side chain are detailed, and their extension to the synthesis of (-)-descarboxamidopyrimidoblamic acid (4) is described.