Ethyl (2R,3S,4S,5S,6S)-8-azido-4,5-epoxy-2,3,6-trihydroxyoctanoate | 151953-15-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Ethyl (2R,3S,4S,5S,6S)-8-azido-4,5-epoxy-2,3,6-trihydroxyoctanoate
• 英文别名: ethyl (2R,3R)-3-[(2S,3S)-3-[(1S)-3-azido-1-hydroxypropyl]oxiran-2-yl]-2,3-dihydroxypropanoate
• CAS: 151953-15-0
• 化学式: C₁₀H₁₇N₃O₆
• 分子量: 275.261
• InChiKey: VLCKEFHBBZQLFV-ABRLLLAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Ethyl (2R,3S,4S,5S,6S)-8-azido-4,5-epoxy-2,3,6-trihydroxyoctanoate 在 palladium on activated charcoal 吡啶 、 dimethyl sulfide borane 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 108.0h， 生成 Castanospermine tetraacetate
  参考文献：
  名称：

  A concise, enantioselective synthesis of castanospermine

  摘要：

  A stereoselective synthesis of the polyhydroxy indolizidine alkaloids castanospermine (1) and 6,7-diepicastanospermine (4) has been achieved starting from the readily available alcohol 8. Subsequent Sharpless asymmetric epoxidation, followed by the azide displacement of the tosyl group gave the epoxy azide 12. The asymmetric dihydroxylation of 12 with (DHQ)2-PHAL gave the triol 13 in good diastereoselectivity. Alcohol protection, followed by reductive double cyclization of the resulting epoxy azide 17 gave 5-indolizidinone 18, which was then uneventfully converted to 1. On the other hand, the use of (DHQD)2-PHAL in the dihydroxylation of 12 provided a stereoselective preparation of 4.

  DOI：

  10.1021/jo00077a034
• 作为产物：
  描述：

  Ethyl (4S,5S,6S)-8-azido-4,5-epoxy-6-hydroxy-(E)-2-octenoate 在 potassium osmate(VI) 、 甲基磺酰胺 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 12.0h， 生成 Ethyl (2R,3S,4S,5S,6S)-8-azido-4,5-epoxy-2,3,6-trihydroxyoctanoate 、 Ethyl (2S,3R,4S,5S,6S)-8-azido-4,5-epoxy-2,3,6-trihydroxyoctanoate
  参考文献：
  名称：

  A concise, enantioselective synthesis of castanospermine

  摘要：

  A stereoselective synthesis of the polyhydroxy indolizidine alkaloids castanospermine (1) and 6,7-diepicastanospermine (4) has been achieved starting from the readily available alcohol 8. Subsequent Sharpless asymmetric epoxidation, followed by the azide displacement of the tosyl group gave the epoxy azide 12. The asymmetric dihydroxylation of 12 with (DHQ)2-PHAL gave the triol 13 in good diastereoselectivity. Alcohol protection, followed by reductive double cyclization of the resulting epoxy azide 17 gave 5-indolizidinone 18, which was then uneventfully converted to 1. On the other hand, the use of (DHQD)2-PHAL in the dihydroxylation of 12 provided a stereoselective preparation of 4.

  DOI：

  10.1021/jo00077a034