(1R,2R,3R,7S,7aR)-1,2-bis(benzyloxy)-3-benzyloxymethyl-7-hydroxypyrrolizidin-5-one | 1357007-93-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2R,3R,7S,7aR)-1,2-bis(benzyloxy)-3-benzyloxymethyl-7-hydroxypyrrolizidin-5-one
• CAS: 1357007-93-2
• 化学式: C₂₉H₃₁NO₅
• 分子量: 473.569
• InChiKey: DVUMORNLJDADTG-UNKNUIIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  68.23
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R,7S,7aR)-1,2-bis(benzyloxy)-3-benzyloxymethyl-7-hydroxypyrrolizidin-5-one 在 borane-dimethyl sulfide complex 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以87%的产率得到(1R,2R,3R,7S,7aR)-1,2-dibenzyloxy-3-benzyloxymethyl-7-hydroxy-2,3,5,6,7,7a-hexahydro-1H-pyrrolizine
  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：

  (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