(4S,4aS)-3-((S)-2-(benzyloxy)-1-iodoethyl)-1-oxohexahydro-1H-pyrrolo[1,2-c][1,3]oxazin-4-yl pivalate | 1198580-18-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,4aS)-3-((S)-2-(benzyloxy)-1-iodoethyl)-1-oxohexahydro-1H-pyrrolo[1,2-c][1,3]oxazin-4-yl pivalate
• CAS: 1198580-18-5
• 化学式: C₂₁H₂₈INO₅
• 分子量: 501.362
• InChiKey: IWRAEHGFBUGJTL-XSLAGTTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4S,4aS)-3-((S)-2-(benzyloxy)-1-iodoethyl)-1-oxohexahydro-1H-pyrrolo[1,2-c][1,3]oxazin-4-yl pivalate 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 以59%的产率得到(3S,4S,4aS)-3-(2-(benzyloxy)ethyl)-1-oxohexahydro-1H-pyrrolo[1,2-c][1,3]oxazin-4-yl pivalate
  参考文献：
  名称：

  Polyhydroxylated indolizidine alkaloids—synthesis of dideoxycastanospermine

  摘要：

  The key transformation developed in this work is the anti-Kishi selective dihydroxylation, which proceeds by way of intramolecular participation of the nitrogen protecting group to furnish the desired stereochemistry required for castanospermine like structures. In this paper, we completed a first synthesis of a novel dideoxycastanospermine 6. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.017
• 作为产物：
  描述：

  tert-butyl (S)-2-((R,E)-4-(benzyloxy)-1-(pivaloyloxy)but-2-enyl)pyrrolidine-1-carboxylate 在 碘 、 silver(I) acetate 、 溶剂黄146 作用下， 以55%的产率得到(4S,4aS)-3-((S)-2-(benzyloxy)-1-iodoethyl)-1-oxohexahydro-1H-pyrrolo[1,2-c][1,3]oxazin-4-yl pivalate
  参考文献：
  名称：

  Polyhydroxylated indolizidine alkaloids—synthesis of dideoxycastanospermine

  摘要：

  The key transformation developed in this work is the anti-Kishi selective dihydroxylation, which proceeds by way of intramolecular participation of the nitrogen protecting group to furnish the desired stereochemistry required for castanospermine like structures. In this paper, we completed a first synthesis of a novel dideoxycastanospermine 6. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.017