(6R,7R,8R,8aS)-6,7-O-Isopropylidene-6,7,8-trihydroxyindolizidine | 141116-88-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (6R,7R,8R,8aS)-6,7-O-Isopropylidene-6,7,8-trihydroxyindolizidine
• 英文别名: (3aR,8aS,9R,9aR)-2,2-dimethyl-3a,4,6,7,8,8a,9,9a-octahydro-[1,3]dioxolo[4,5-f]indolizin-9-ol
• CAS: 141116-88-3
• 化学式: C₁₁H₁₉NO₃
• 分子量: 213.277
• InChiKey: MUSBUHVMKWYQIF-JLIMGVALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6R,7R,8R,8aS)-6,7-O-Isopropylidene-6,7,8-trihydroxyindolizidine 在 水 、 三氟乙酸 作用下， 反应 50.0h， 生成 (-)-(6R,7S,8R,8aS)-6,7,8-trihydroxyindolizidine
  参考文献：
  名称：

  Synthesis of 1-deoxycastanospermine and stereoisomers

  摘要：

  Four different isomers of 1-deoxycastanospermine (6,7,8-trihydroxyindolizidine) were synthesized. Their basic skeleton was constructed from a proline derivative and the anion of allyl phenyl sulfide, followed by an allylic sulfide rearrangement and a subsequent nucleophilic cyclization. The aminotriols were obtained in good yields with a concise overall sequence.

  DOI：

  10.1021/jo00037a025
• 作为产物：
  描述：

  (2S)-N-苄氧羰基-2-吡咯烷甲醛 在 四氯化碳 、 sodium hydroxide 、 四氧化锇 、 camphor-10-sulfonic acid 、 potassium carbonate 、 N-甲基吗啉氧化物 、 间氯过氧苯甲酸 、 三苯基膦 、 三甲氧基磷 作用下， 以 甲醇 、 二氯甲烷 、 水 、 异丙醇 、 丙酮 、 叔丁醇 为溶剂， 反应 61.0h， 生成 (6R,7R,8R,8aS)-6,7-O-Isopropylidene-6,7,8-trihydroxyindolizidine
  参考文献：
  名称：

  Synthesis of 1-deoxycastanospermine and stereoisomers

  摘要：

  Four different isomers of 1-deoxycastanospermine (6,7,8-trihydroxyindolizidine) were synthesized. Their basic skeleton was constructed from a proline derivative and the anion of allyl phenyl sulfide, followed by an allylic sulfide rearrangement and a subsequent nucleophilic cyclization. The aminotriols were obtained in good yields with a concise overall sequence.

  DOI：

  10.1021/jo00037a025

文献信息

• Synthesis of 1-deoxycastanospermine and stereoisomers
  作者：Yves St-Denis、Tak Hang Chan

  DOI：10.1021/jo00037a025

  日期：1992.5

  Four different isomers of 1-deoxycastanospermine (6,7,8-trihydroxyindolizidine) were synthesized. Their basic skeleton was constructed from a proline derivative and the anion of allyl phenyl sulfide, followed by an allylic sulfide rearrangement and a subsequent nucleophilic cyclization. The aminotriols were obtained in good yields with a concise overall sequence.