(2S,3S,5R,6R,7S,7aS)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-2-ol | 1454681-24-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (2S,3S,5R,6R,7S,7aS)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-2-ol
• CAS: 1454681-24-3
• 化学式: C₃₀H₃₅NO₄
• 分子量: 473.612
• InChiKey: SEHNCOFDFSKVBK-LBNUKBDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 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：
  0.4
• 拓扑面积：
  51.16
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,5R,6R,7S,7aS)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-2-ol 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以90%的产率得到(1S,2R,3R,5S,6S,7aS)-3-(hydroxymethyl)-5-methylhexahydro-1H-pyrrolizine-1,2,6-triol
  参考文献：
  名称：

  A sort synthesis of polyhydroxylated pyrrolizidines via sequential 1,3-dipolar cycloaddition and reductive amination

  摘要：

  Polyhydroxylated pyrrolizidines bearing a methyl group at C-5 have been synthesized by 1,3-dipolar cycloaddition of five membered cyclic nitrones with methyl vinyl ketone followed by a N-O reductive cleavage and in situ intramolecular reductive amination. The stereochemistry of the obtained compounds is examined in relation to the reactions mechanism. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.098
• 作为产物：
  描述：

  1-[((2S, 3aS, 4S, 5R, 6R)-4,5-bis(benzyloxy)-6-benzyloxymethyl)hexahydropyrrolo[1,2-b]isoxazol-2-yl]ethanone 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 以83%的产率得到(2S,3S,5R,6R,7S,7aS)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-2-ol
  参考文献：
  名称：

  A sort synthesis of polyhydroxylated pyrrolizidines via sequential 1,3-dipolar cycloaddition and reductive amination

  摘要：

  Polyhydroxylated pyrrolizidines bearing a methyl group at C-5 have been synthesized by 1,3-dipolar cycloaddition of five membered cyclic nitrones with methyl vinyl ketone followed by a N-O reductive cleavage and in situ intramolecular reductive amination. The stereochemistry of the obtained compounds is examined in relation to the reactions mechanism. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.098