(3S,4S,4aS)-3-(2-(benzyloxy)ethyl)-4-(methoxymethoxy)hexahydro-1H-pyrrolo[1,2-c][1,3]oxazin-1-one | 1198580-26-5

• 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: (3S,4S,4aS)-3-(2-(benzyloxy)ethyl)-4-(methoxymethoxy)hexahydro-1H-pyrrolo[1,2-c][1,3]oxazin-1-one
• 英文别名: (3S,4S,4aS)-4-(methoxymethoxy)-3-(2-phenylmethoxyethyl)-3,4,4a,5,6,7-hexahydropyrrolo[1,2-c][1,3]oxazin-1-one
• CAS: 1198580-26-5
• 化学式: C₁₈H₂₅NO₅
• 分子量: 335.4
• InChiKey: AQHPOAUBUZNSCE-ULQDDVLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4S,4aS)-3-(2-(benzyloxy)ethyl)-4-(methoxymethoxy)hexahydro-1H-pyrrolo[1,2-c][1,3]oxazin-1-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以93%的产率得到(3S,4S,4aS)-3-(2-hydroxyethyl)-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：

  (3R,4S,4aS)-3-((S)-2-(benzyloxy)-1-iodoethyl)-4-(methoxymethoxy)hexahydro-1H-pyrrolo[1,2-c][1,3]oxazin-1-one 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 以77%的产率得到(3S,4S,4aS)-3-(2-(benzyloxy)ethyl)-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

文献信息

• Polyhydroxylated indolizidine alkaloids—synthesis of dideoxycastanospermine
  作者：Ari M.P. Koskinen、Oili A. Kallatsa、Maija Nissinen

  DOI：10.1016/j.tet.2009.09.017

  日期：2009.11

  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.