(2R,3S)-methyl 2-[(benzyloxy)methyl]-3-[(tert-butyldimethylsilyl)oxy]-4-methylene-5-oxopyrrolidine-2-carboxylate | 1002321-64-3

• 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: (2R,3S)-methyl 2-[(benzyloxy)methyl]-3-[(tert-butyldimethylsilyl)oxy]-4-methylene-5-oxopyrrolidine-2-carboxylate
• 英文别名: methyl (2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-4-methylidene-5-oxo-2-(phenylmethoxymethyl)pyrrolidine-2-carboxylate
• CAS: 1002321-64-3
• 化学式: C₂₁H₃₁NO₅Si
• 分子量: 405.566
• InChiKey: JHJMVWUXKDEHCE-LAUBAEHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S)-methyl 2-[(benzyloxy)methyl]-3-[(tert-butyldimethylsilyl)oxy]-4-methylene-5-oxopyrrolidine-2-carboxylate 、 4-甲氧基溴苄 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以92%的产率得到(2R,3S)-methyl 2-benzyloxymethyl-3-tert-butyldimethylsilyloxy-1-(4-methoxybenzyl)-4-methylene-5-oxopyrrolidine-2-carboxylate
  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：

  (2R,3S)-methyl 2-[(benzyloxy)methyl]-3-hydroxy-4-methylene-5-oxopyrrolidine-2-carboxylate 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以97%的产率得到(2R,3S)-methyl 2-[(benzyloxy)methyl]-3-[(tert-butyldimethylsilyl)oxy]-4-methylene-5-oxopyrrolidine-2-carboxylate
  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.