(3aRS,6RS,6aSR)-5-tert-butyl 6-methyl 6-[(benzyloxy)methyl]-2-methyl-4-oxohexahydro-5H-pyrrolo[3,4-d]isoxazole-5,6-dicarboxylate

• 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: (3aRS,6RS,6aSR)-5-tert-butyl 6-methyl 6-[(benzyloxy)methyl]-2-methyl-4-oxohexahydro-5H-pyrrolo[3,4-d]isoxazole-5,6-dicarboxylate
• 英文别名: 5-O-tert-butyl 6-O-methyl (3aR,6R,6aS)-2-methyl-4-oxo-6-(phenylmethoxymethyl)-3a,6a-dihydro-3H-pyrrolo[3,4-d][1,2]oxazole-5,6-dicarboxylate
• 化学式: C₂₁H₂₈N₂O₇
• 分子量: 420.463
• InChiKey: PUMKBWNJLQXCAL-VWKPWSFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  94.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3aRS,6RS,6aSR)-5-tert-butyl 6-methyl 6-[(benzyloxy)methyl]-2-methyl-4-oxohexahydro-5H-pyrrolo[3,4-d]isoxazole-5,6-dicarboxylate 在 palladium dihydroxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Nitrone [2+3]-Cycloadditions in Stereocontrolled Synthesis of a Potent Proteasome Inhibitor:  (−)-Omuralide

  摘要：

  A new stereocontrolled synthetic route to omuralide has been developed from methyl pyroglutamate. This route involves regio- and stereoselective N-methylnitrone 1,3-dipolar cycloadditions to appropriate pyrrolinones, beta-eliminations, and highly selective hydrogenations as the main steps.

  DOI：

  10.1021/jo701968d
• 作为产物：
  描述：

  (S)-1-tert-butyl 2-methyl 2-[(benzyloxy)methyl]-5-oxo-1H-pyrrole-1,2-(2H,5H)-dicarboxylate 、 N-methylnitrone 以 甲苯 为溶剂， 反应 2.2h， 以89%的产率得到(3aRS,6RS,6aSR)-5-tert-butyl 6-methyl 6-[(benzyloxy)methyl]-2-methyl-4-oxohexahydro-5H-pyrrolo[3,4-d]isoxazole-5,6-dicarboxylate
  参考文献：
  名称：

  Nitrone [2+3]-Cycloadditions in Stereocontrolled Synthesis of a Potent Proteasome Inhibitor:  (−)-Omuralide

  摘要：

  A new stereocontrolled synthetic route to omuralide has been developed from methyl pyroglutamate. This route involves regio- and stereoselective N-methylnitrone 1,3-dipolar cycloadditions to appropriate pyrrolinones, beta-eliminations, and highly selective hydrogenations as the main steps.

  DOI：

  10.1021/jo701968d

文献信息

• Nitrone [2+3]-Cycloadditions in Stereocontrolled Synthesis of a Potent Proteasome Inhibitor:  (−)-Omuralide
  作者：Jean-Christophe Legeay、Nicole Langlois

  DOI：10.1021/jo701968d

  日期：2007.12.1

  A new stereocontrolled synthetic route to omuralide has been developed from methyl pyroglutamate. This route involves regio- and stereoselective N-methylnitrone 1,3-dipolar cycloadditions to appropriate pyrrolinones, beta-eliminations, and highly selective hydrogenations as the main steps.