(3R,4S,5S)-3,4-dihydroxy-8-oxa-1-azabicyclo[3.2.1]octane | 848862-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: (3R,4S,5S)-3,4-dihydroxy-8-oxa-1-azabicyclo[3.2.1]octane
• 英文别名: (3R,4S,5S)-8-oxa-1-azabicyclo[3.2.1]octane-3,4-diol
• CAS: 848862-10-2
• 化学式: C₆H₁₁NO₃
• 分子量: 145.158
• InChiKey: LNDMGNWELXCNBB-SRQIZXRXSA-N

物化性质

• 沸点：
  243.9±50.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S)-3,4-dihydroxy-8-oxa-1-azabicyclo[3.2.1]octane 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以99%的产率得到(3R,4R,5S)-3,4,5-trihydroxyazepane
  参考文献：
  名称：

  Synthesis of a trihydroxylated azepane from d-arabinose by way of an intramolecular alkene nitrone cycloaddition

  摘要：

  The synthesis of 1,6-imino-1,5,6-trideoxy-(L)-xylo-hexitol, a trihydroxylated azepane, from (D)-arabinose was achieved by way of an intramolecular alkene nitrone cycloaddition. The final product as well as its bicyclic precursor, (3R,4S,5S)-3,4-dihydroxy-8-oxa-1-azabicyclo[3.2.1]octane, were evaluated as glycosidase inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.041
• 作为产物：
  描述：

  (3R,4S,5S)-3,4-dibenzoyloxy-8-oxa-1-azabicyclo[3.2.1]octane 在 甲醇 、 sodium methylate 作用下， 反应 2.0h， 以81%的产率得到(3R,4S,5S)-3,4-dihydroxy-8-oxa-1-azabicyclo[3.2.1]octane
  参考文献：
  名称：

  Synthesis of a trihydroxylated azepane from d-arabinose by way of an intramolecular alkene nitrone cycloaddition

  摘要：

  The synthesis of 1,6-imino-1,5,6-trideoxy-(L)-xylo-hexitol, a trihydroxylated azepane, from (D)-arabinose was achieved by way of an intramolecular alkene nitrone cycloaddition. The final product as well as its bicyclic precursor, (3R,4S,5S)-3,4-dihydroxy-8-oxa-1-azabicyclo[3.2.1]octane, were evaluated as glycosidase inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.041

文献信息

• Synthesis of a trihydroxylated azepane from d-arabinose by way of an intramolecular alkene nitrone cycloaddition
  作者：Stéphane Moutel、Michael Shipman、Olivier R. Martin、Kyoko Ikeda、Naoki Asano

  DOI：10.1016/j.tetasy.2004.11.041

  日期：2005.1

  The synthesis of 1,6-imino-1,5,6-trideoxy-(L)-xylo-hexitol, a trihydroxylated azepane, from (D)-arabinose was achieved by way of an intramolecular alkene nitrone cycloaddition. The final product as well as its bicyclic precursor, (3R,4S,5S)-3,4-dihydroxy-8-oxa-1-azabicyclo[3.2.1]octane, were evaluated as glycosidase inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.