(3S,6R,7R,8R,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-6,7,8-trihydroxyindolizidin-5-one | 244274-71-3

• 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: (3S,6R,7R,8R,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-6,7,8-trihydroxyindolizidin-5-one
• 英文别名: (3S,6R,7R,8R,8aS)-3-[[tert-butyl(diphenyl)silyl]oxymethyl]-6,7,8-trihydroxy-2,3,6,7,8,8a-hexahydro-1H-indolizin-5-one
• CAS: 244274-71-3
• 化学式: C₂₅H₃₃NO₅Si
• 分子量: 455.626
• InChiKey: KKELLSIECOEXKT-AZCFJWIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.02
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  90.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,6R,7R,8R,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-6,7,8-trihydroxyindolizidin-5-one 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 dimethyl sulfide borane 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 25.0h， 生成 (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 potassium permanganate 、 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 、 叔丁基二甲硅基三氟甲磺酸酯 、 dicyclohexano-18-crown-6 、 苯硫酚 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 (3S,6R,7R,8R,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-6,7,8-trihydroxyindolizidin-5-one
  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