(3S,8S,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-8-(tert-butyldimethylsilyloxy)indolizidin-5-one | 244274-69-9

• 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,8S,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-8-(tert-butyldimethylsilyloxy)indolizidin-5-one
• 英文别名: (3S,8S,8aS)-8-[tert-butyl(dimethyl)silyl]oxy-3-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,3,6,7,8,8a-hexahydro-1H-indolizin-5-one
• CAS: 244274-69-9
• 化学式: C₃₁H₄₇NO₃Si₂
• 分子量: 537.89
• InChiKey: CEQSXKCGMWRQGQ-WIRXVTQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.11
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,8S,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-8-(tert-butyldimethylsilyloxy)indolizidin-5-one 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以71%的产率得到(3S,8S,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-indolizine
  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 palladium on activated charcoal 咪唑 、 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 、 氢气 、 sodium methylate 、 sodium acetate 、 苯硫酚 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 63.5h， 生成 (3S,8S,8aS)-3-(tert-butyldiphenylsilyloxymethyl)-8-(tert-butyldimethylsilyloxy)indolizidin-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