(3S,4S,4aS)-3-(2-hydroxyethyl)-4-(methoxymethoxy)hexahydro-1H-pyrrolo[1,2-c][1,3]oxazin-1-one | 1198580-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (3S,4S,4aS)-3-(2-hydroxyethyl)-4-(methoxymethoxy)hexahydro-1H-pyrrolo[1,2-c][1,3]oxazin-1-one
• 英文别名: (3S,4S,4aS)-3-(2-hydroxyethyl)-4-(methoxymethoxy)-3,4,4a,5,6,7-hexahydropyrrolo[1,2-c][1,3]oxazin-1-one
• CAS: 1198580-27-6
• 化学式: C₁₁H₁₉NO₅
• 分子量: 245.276
• InChiKey: WUHXHWCFYZZXHR-GUBZILKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4S,4aS)-3-(2-hydroxyethyl)-4-(methoxymethoxy)hexahydro-1H-pyrrolo[1,2-c][1,3]oxazin-1-one 在 四氯化碳 、 potassium carbonate 、 三苯基膦 作用下， 以 乙腈 为溶剂， 以63%的产率得到(3S,4S,4aS)-3-(2-chloroethyl)-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：

  (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

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.