methyl 2-[(2S,3R)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]pyrrolidin-2-yl]acetate | 207113-34-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: methyl 2-[(2S,3R)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]pyrrolidin-2-yl]acetate
• CAS: 207113-34-6
• 化学式: C₁₉H₄₁NO₄Si₂
• 分子量: 403.71
• InChiKey: CHEMJZYOXXGUCI-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-[(2S,3R)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]pyrrolidin-2-yl]acetate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 生成 benzyl (3aR,6aR)-2-oxo-3a,5,6,6a-tetrahydro-3H-furo[3,2-b]pyrrole-4-carboxylate
  参考文献：
  名称：

  Synthesis of (R)- and (S)-3-(tert-butyldimethylsilyloxy)-1-pyrroline N-oxides — chiral nitrones for synthesis of biologically active pyrrolidine derivative, Geissman-Waiss lactone

  摘要：

  Tungstate-catalyzed oxidation of O-tert-butyldimethylsilyl (O-TBDMS) protected (R)-3-hydroxypyrrolidine ((R)-2), derived from trans-4-hydroxy-L-proline, gave O-TBDMS protected (R)-3-hydroxy-1-pyrroline N-oxide ((R)-1), which is a new chiral precursor for the synthesis of Geissman-Waiss lactone. The enantiomeric nitrone (S)-1 was also prepared by the oxidation of (S)-2 derived from L-malic acid. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00333-5
• 作为产物：
  描述：

  (R)-3-((tert-butyldimethylsilyl)oxy)pyrrolidine 在 sodium tungstate 、 四丁基氯化铵 、 双氧水 、 zinc(II) iodide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.5h， 生成 methyl 2-[(2S,3R)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]pyrrolidin-2-yl]acetate
  参考文献：
  名称：

  Synthesis of (R)- and (S)-3-(tert-butyldimethylsilyloxy)-1-pyrroline N-oxides — chiral nitrones for synthesis of biologically active pyrrolidine derivative, Geissman-Waiss lactone

  摘要：

  Tungstate-catalyzed oxidation of O-tert-butyldimethylsilyl (O-TBDMS) protected (R)-3-hydroxypyrrolidine ((R)-2), derived from trans-4-hydroxy-L-proline, gave O-TBDMS protected (R)-3-hydroxy-1-pyrroline N-oxide ((R)-1), which is a new chiral precursor for the synthesis of Geissman-Waiss lactone. The enantiomeric nitrone (S)-1 was also prepared by the oxidation of (S)-2 derived from L-malic acid. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00333-5

文献信息

• Synthesis of (R)- and (S)-3-(tert-butyldimethylsilyloxy)-1-pyrroline N-oxides — chiral nitrones for synthesis of biologically active pyrrolidine derivative, Geissman-Waiss lactone
  作者：Shun-Ichi Murahashi、Hiroaki Ohtake、Yasushi Imada

  DOI：10.1016/s0040-4039(98)00333-5

  日期：1998.4

  Tungstate-catalyzed oxidation of O-tert-butyldimethylsilyl (O-TBDMS) protected (R)-3-hydroxypyrrolidine ((R)-2), derived from trans-4-hydroxy-L-proline, gave O-TBDMS protected (R)-3-hydroxy-1-pyrroline N-oxide ((R)-1), which is a new chiral precursor for the synthesis of Geissman-Waiss lactone. The enantiomeric nitrone (S)-1 was also prepared by the oxidation of (S)-2 derived from L-malic acid. (C) 1998 Elsevier Science Ltd. All rights reserved.