(1R,2R,3R,7S,7aS)-1,2-bis(benzyloxy)-3-benzyloxymethyl-7-(dimethylphenylsilyl)pyrrolizidin-5-one | 1357007-89-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯里西啶类
• 英文名称: (1R,2R,3R,7S,7aS)-1,2-bis(benzyloxy)-3-benzyloxymethyl-7-(dimethylphenylsilyl)pyrrolizidin-5-one
• 英文别名: (1S,5R,6R,7R,8S)-1-[dimethyl(phenyl)silyl]-6,7-bis(phenylmethoxy)-5-(phenylmethoxymethyl)-1,2,5,6,7,8-hexahydropyrrolizin-3-one
• CAS: 1357007-89-6
• 化学式: C₃₇H₄₁NO₄Si
• 分子量: 591.822
• InChiKey: SVFILCDLEHPLOR-VSNXSOFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.34
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R,7S,7aS)-1,2-bis(benzyloxy)-3-benzyloxymethyl-7-(dimethylphenylsilyl)pyrrolizidin-5-one 在 过氧化氢异丙苯 、 四丁基氟化铵 、 potassium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以57%的产率得到(1R,2R,3R,7S,7aR)-1,2-bis(benzyloxy)-3-benzyloxymethyl-7-hydroxypyrrolizidin-5-one
  参考文献：
  名称：

  SmI₂-Mediated Cross-Coupling of Nitrones with β-Silyl Acrylates: Synthesis of (+)-Australine

  摘要：

  The SmI2-mediated cross-coupling of nitrones with beta-silyl-alpha,beta-unsaturated esters, followed by zinc reduction, allows an efficient and highly diastereoselective preparation of beta-silyl lactams, which are precursors of beta-hydroxy lactams through Tamao-Fleming oxidation. By applying the method to a cyclic, carbohydrate-derived nitrone, a new synthesis of (+)-australine has been realized in only 11 steps and in 21% overall yield from L-xylose.

  DOI：

  10.1021/ol203396s
• 作为产物：
  描述：

  ethyl (E)-3-dimethylphenylsilyl-2-propenoate 、 (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide 在 samarium diiodide 、 六氟异丙醇 、 lithium bromide 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 0.1h， 以64%的产率得到(1R,2R,3R,7S,7aS)-1,2-bis(benzyloxy)-3-benzyloxymethyl-7-(dimethylphenylsilyl)pyrrolizidin-5-one
  参考文献：
  名称：

  SmI₂-Mediated Cross-Coupling of Nitrones with β-Silyl Acrylates: Synthesis of (+)-Australine

  摘要：

  The SmI2-mediated cross-coupling of nitrones with beta-silyl-alpha,beta-unsaturated esters, followed by zinc reduction, allows an efficient and highly diastereoselective preparation of beta-silyl lactams, which are precursors of beta-hydroxy lactams through Tamao-Fleming oxidation. By applying the method to a cyclic, carbohydrate-derived nitrone, a new synthesis of (+)-australine has been realized in only 11 steps and in 21% overall yield from L-xylose.

  DOI：

  10.1021/ol203396s

文献信息

• SmI₂-Mediated Cross-Coupling of Nitrones with β-Silyl Acrylates: Synthesis of (+)-Australine
  作者：Pierre Gilles、Sandrine Py

  DOI：10.1021/ol203396s

  日期：2012.2.17

  The SmI2-mediated cross-coupling of nitrones with beta-silyl-alpha,beta-unsaturated esters, followed by zinc reduction, allows an efficient and highly diastereoselective preparation of beta-silyl lactams, which are precursors of beta-hydroxy lactams through Tamao-Fleming oxidation. By applying the method to a cyclic, carbohydrate-derived nitrone, a new synthesis of (+)-australine has been realized in only 11 steps and in 21% overall yield from L-xylose.