(2R,3S)-methyl 2-benzyloxymethyl-3-tert-butyldimethylsilyloxy-1-(4-methoxybenzyl)-4-methylene-5-oxopyrrolidine-2-carboxylate | 1002321-67-6

• 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-benzyloxymethyl-3-tert-butyldimethylsilyloxy-1-(4-methoxybenzyl)-4-methylene-5-oxopyrrolidine-2-carboxylate
• 英文别名: methyl (2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-1-[(4-methoxyphenyl)methyl]-4-methylidene-5-oxo-2-(phenylmethoxymethyl)pyrrolidine-2-carboxylate
• CAS: 1002321-67-6
• 化学式: C₂₉H₃₉NO₆Si
• 分子量: 525.717
• InChiKey: WXLWCGWVANBROY-ABYGYWHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S)-methyl 2-benzyloxymethyl-3-tert-butyldimethylsilyloxy-1-(4-methoxybenzyl)-4-methylene-5-oxopyrrolidine-2-carboxylate 在 platinum(IV) oxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.5h， 以89%的产率得到(2R,3S,4R)-methyl 2-benzyloxymethyl-3-tert-butyldimethylsilyloxy-1-(4-methoxybenzyl)-4-methyl-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-[(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

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.