(3S,6S,7S,8R,8aS)-6,7,8-trihydroxy-3-(hydroxymethyl)indolizidine | 244274-68-8

• 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: (3S,6S,7S,8R,8aS)-6,7,8-trihydroxy-3-(hydroxymethyl)indolizidine
• 英文别名: (3S,6S,7S,8R,8aS)-3-(hydroxymethyl)-1,2,3,5,6,7,8,8a-octahydroindolizine-6,7,8-triol
• CAS: 244274-68-8
• 化学式: C₉H₁₇NO₄
• 分子量: 203.238
• InChiKey: IUPGFGRLPXGNOB-XRBOHMRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (3S,6S,7S,8R,8aS)-6,7,8-trihydroxy-3-(hydroxymethyl)indolizidine 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 12.0h， 以90%的产率得到(3S,6S,7S,8R,8aS)-6,7,8-triacetoxy-3-(acetoxymethyl)indolizidine
  参考文献：
  名称：

  Lewis Acid Assisted Vinylogous Mannich and Mukaiyama Aldol Reactions: A Route to Densely Hydroxylated Indolizidine Alkaloid Analogues

  摘要：

  The hydroxymethyl-substituted indolizidines 6 and 7, representative members of a ring-B-expanded alexine- australine subclass, are readily accessible by starting with furan-based silyloxydiene 12 and hydroxymethyl hemiaminal 11, through a synthesis sequence involving a scantily exploited vinylogous version of the Mannich reaction. The key iminium electrophilic acceptor 11 is, in turn, available through a vinylogous intermolecular Mukaiyama aldolization process between pyrrole-based silyloxydiene 8 and (S)-glyceraldehyde 9.

  DOI：

  10.1002/(sici)1099-0690(199906)1999:6<1395::aid-ejoc1395>3.0.co;2-t
• 作为产物：
  描述：

  N-tert-butyloxycarbonyl(5-diphenyl-tert-butylsilyloxymethyl)-2-hydroxypyrrolidine 在 吡啶 、 盐酸 、 potassium permanganate 、 三氟甲磺酸三甲基硅酯 、 dimethyl sulfide borane 、 三氟化硼乙醚 、 叔丁基二甲硅基三氟甲磺酸酯 、 水 、 dicyclohexano-18-crown-6 、 苯硫酚 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 19.5h， 生成 (3S,6S,7S,8R,8aS)-6,7,8-trihydroxy-3-(hydroxymethyl)indolizidine
  参考文献：
  名称：

  Lewis Acid Assisted Vinylogous Mannich and Mukaiyama Aldol Reactions: A Route to Densely Hydroxylated Indolizidine Alkaloid Analogues

  摘要：

  The hydroxymethyl-substituted indolizidines 6 and 7, representative members of a ring-B-expanded alexine- australine subclass, are readily accessible by starting with furan-based silyloxydiene 12 and hydroxymethyl hemiaminal 11, through a synthesis sequence involving a scantily exploited vinylogous version of the Mannich reaction. The key iminium electrophilic acceptor 11 is, in turn, available through a vinylogous intermolecular Mukaiyama aldolization process between pyrrole-based silyloxydiene 8 and (S)-glyceraldehyde 9.

  DOI：

  10.1002/(sici)1099-0690(199906)1999:6<1395::aid-ejoc1395>3.0.co;2-t

文献信息

• Lewis Acid Assisted Vinylogous Mannich and Mukaiyama Aldol Reactions: A Route to Densely Hydroxylated Indolizidine Alkaloid Analogues
  作者：Gloria Rassu、Paola Carta、Luigi Pinna、Lucia Battistini、Franca Zanardi、Domenico Acquotti、Giovanni Casiraghi

  DOI：10.1002/(sici)1099-0690(199906)1999:6<1395::aid-ejoc1395>3.0.co;2-t

  日期：1999.6

  The hydroxymethyl-substituted indolizidines 6 and 7, representative members of a ring-B-expanded alexine- australine subclass, are readily accessible by starting with furan-based silyloxydiene 12 and hydroxymethyl hemiaminal 11, through a synthesis sequence involving a scantily exploited vinylogous version of the Mannich reaction. The key iminium electrophilic acceptor 11 is, in turn, available through a vinylogous intermolecular Mukaiyama aldolization process between pyrrole-based silyloxydiene 8 and (S)-glyceraldehyde 9.