methyl (3R,7S,7aR)-3-tert-butyl-7-hydroxy-7-methyl-6-methylidene-5-oxo-1,3-dihydropyrrolo[1,2-c][1,3]oxazole-7a-carboxylate | 1228700-69-3

• 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 (3R,7S,7aR)-3-tert-butyl-7-hydroxy-7-methyl-6-methylidene-5-oxo-1,3-dihydropyrrolo[1,2-c][1,3]oxazole-7a-carboxylate
• CAS: 1228700-69-3
• 化学式: C₁₄H₂₁NO₅
• 分子量: 283.324
• InChiKey: XZJVMGDYJCZPBL-SWHYSGLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl (3R,6R,7S,7aR)-3-tert-butyl-7-hydroxy-6-(hydroxymethyl)-7-methyl-5-oxo-3,6-dihydro-1H-pyrrolo[1,2-c][1,3]oxazole-7a-carboxylate 在 咪唑 、 碘 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以90%的产率得到methyl (3R,7S,7aR)-3-tert-butyl-7-hydroxy-7-methyl-6-methylidene-5-oxo-1,3-dihydropyrrolo[1,2-c][1,3]oxazole-7a-carboxylate
  参考文献：
  名称：

  Concise Formal Synthesis of (−)-Salinosporamide A (Marizomib) Using a Regio- and Stereoselective Epoxidation and Reductive Oxirane Ring-Opening Strategy

  摘要：

  Expedient access to a highly functionalized 2-pyrrolidinone (8). the gamma-lactam core of 20S proteasome inhibitor (-)-salinosporamide A (marizomib; NPI-0052; 1), using a regio- and stereoselective epoxide formation/reductive oxirane ring-opening strategy is presented. Notably, the sequential construction of the C-4, C-3, and C-2 stereocenters of 1 in a completely stereocontrolled fashion is a key feature of streamlining the synthesis of intermediate 12. A related strategy is also discussed.

  DOI：

  10.1021/jo100432g