methyl (3R,6R,7R,7aR)-3-tert-butyl-6,7-dihydroxy-6-(hydroxymethyl)-7-methyl-5-oxo-1,3-dihydropyrrolo[1,2-c][1,3]oxazole-7a-carboxylate | 1228700-66-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: methyl (3R,6R,7R,7aR)-3-tert-butyl-6,7-dihydroxy-6-(hydroxymethyl)-7-methyl-5-oxo-1,3-dihydropyrrolo[1,2-c][1,3]oxazole-7a-carboxylate
• CAS: 1228700-66-0
• 化学式: C₁₄H₂₃NO₇
• 分子量: 317.339
• InChiKey: ZRDXRGNPCCCEMR-QQUHWDOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (3R,6R,7R,7aR)-3-tert-butyl-6,7-dihydroxy-6-(hydroxymethyl)-7-methyl-5-oxo-1,3-dihydropyrrolo[1,2-c][1,3]oxazole-7a-carboxylate 在 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以17 mg的产率得到methyl (3R,6R,7R,7aR)-3-tert-butyl-7-hydroxy-7-methyl-5-oxospiro[1,3-dihydropyrrolo[1,2-c][1,3]oxazole-6,2'-oxirane]-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
• 作为产物：
  描述：

  methyl (3R,7aS)-3-tert-butyl-6-(hydroxymethyl)-7-methyl-5-oxo-1,3-dihydropyrrolo[1,2-c][1,3]oxazole-7a-carboxylate 在 potassium osmate(VI) dihydrate 、 N-甲基吗啉氧化物 、 柠檬酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 15.0h， 生成 methyl (3R,6R,7R,7aR)-3-tert-butyl-6,7-dihydroxy-6-(hydroxymethyl)-7-methyl-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