(3R,4S,4aS)-3-((S)-2-(benzyloxy)-1-iodoethyl)-4-hydroxyhexahydro-1H-pyrrolo[1,2-c][1,3]oxazin-1-one | 1198580-24-3

• 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: (3R,4S,4aS)-3-((S)-2-(benzyloxy)-1-iodoethyl)-4-hydroxyhexahydro-1H-pyrrolo[1,2-c][1,3]oxazin-1-one
• 英文别名: (3R,4S,4aS)-4-hydroxy-3-[(1S)-1-iodo-2-phenylmethoxyethyl]-3,4,4a,5,6,7-hexahydropyrrolo[1,2-c][1,3]oxazin-1-one
• CAS: 1198580-24-3
• 化学式: C₁₆H₂₀INO₄
• 分子量: 417.244
• InChiKey: ARTWVTSEUYFQCN-AJNGGQMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二甲醇缩甲醛 、 (3R,4S,4aS)-3-((S)-2-(benzyloxy)-1-iodoethyl)-4-hydroxyhexahydro-1H-pyrrolo[1,2-c][1,3]oxazin-1-one 在 四磷十氧化物 作用下， 以 氯仿 为溶剂， 以63%的产率得到(3R,4S,4aS)-3-((S)-2-(benzyloxy)-1-iodoethyl)-4-(methoxymethoxy)hexahydro-1H-pyrrolo[1,2-c][1,3]oxazin-1-one
  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：

  (2S,1'R)-N-(tert-butoxycarbonyl)-2-[(4'-benzyloxy-1'-hydroxy)-E-but-2'-enyl]pyrrolidine 在 碘 、 silver(I) acetate 、 溶剂黄146 作用下， 以55%的产率得到(3R,4S,4aS)-3-((S)-2-(benzyloxy)-1-iodoethyl)-4-hydroxyhexahydro-1H-pyrrolo[1,2-c][1,3]oxazin-1-one
  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