(1R*,7S*,8R*,8aS*)-7,8-dihydroxy-1-[(triisopropylsilyl)oxy]indolizidine

• 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: (1R*,7S*,8R*,8aS*)-7,8-dihydroxy-1-[(triisopropylsilyl)oxy]indolizidine
• 英文别名: (1R,7S,8R,8aS)-1-tri(propan-2-yl)silyloxy-1,2,3,5,6,7,8,8a-octahydroindolizine-7,8-diol
• 化学式: C₁₇H₃₅NO₃Si
• 分子量: 329.555
• InChiKey: INOLCDNMEYRQTK-HZMVEIRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R*,7S*,8R*,8aS*)-7,8-dihydroxy-1-[(triisopropylsilyl)oxy]indolizidine 在 盐酸 作用下， 以100%的产率得到(1R*,7S*,8R*,8aR*)-1,7,8-trihydroxyindolizidine
  参考文献：
  名称：

  Efficient stereoselective access to polyhydroxylated indolizidine compounds based on .gamma.-hydroxy-.alpha.,.beta.-unsaturated sulfones

  摘要：

  DOI：

  10.1021/jo00124a002
• 作为产物：
  描述：

  (1R*,7S*,8R*,8aR*)-7-hydroxy-8-(phenylsulfonyl)-1-[(triisopropylsilyl)oxy]indolizidine 在 四氧化锇 sodium amalgam 、 十二/十四烷基二甲基氧化胺 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 生成 (1R*,7S*,8R*,8aS*)-7,8-dihydroxy-1-[(triisopropylsilyl)oxy]indolizidine
  参考文献：
  名称：

  Efficient stereoselective access to polyhydroxylated indolizidine compounds based on .gamma.-hydroxy-.alpha.,.beta.-unsaturated sulfones

  摘要：

  DOI：

  10.1021/jo00124a002

文献信息

• Efficient stereoselective access to polyhydroxylated indolizidine compounds based on .gamma.-hydroxy-.alpha.,.beta.-unsaturated sulfones
  作者：Juan C. Carretero、Ramon Gomez Arrayas

  DOI：10.1021/jo00124a002

  日期：1995.9
• Stereoselective Synthesis of Polyhydroxylated Indolizidines from γ-Hydroxy α,β-Unsaturated Sulfones
  作者：Juan C. Carretero、Ramón Gómez Arrayás

  DOI：10.1021/jo972167p

  日期：1998.5.1

  The polyhydroxylated indolizidines castanospermine and swainsonine as well as some of their stereoisomers are powerful glycosidase inhibitors. An efficient and stereochemically flexible synthesis of racemic 1,7,8-trihydroxylated and 1,6,7,8-tetrahydroxylated indolizidines (castanospermine stereoisomers) from readily available N-substituted gamma-oxygenated alpha,beta-unsaturated sulfones 3 and 4 has been developed. The construction of the bicyclic skeleton of 1-hydroxyindolizidine has been accomplished by intramolecular conjugate addition of the nitrogen moiety of 3 and 4 to the alpha,beta-unsaturated sulfone unit to give the pyrrolidine intermediates 5 and 6, followed by formation of the C(7)-C(8) bond by intramolecular acylation (or alkylation) of the alpha-sulfonyl carbanion. The stereoselectivity of the pyrrolidine synthesis was highly dependent on the bulkiness of the gamma-oxygenated function; thus, the free alcohols gave predominantly cis-pyrrolidines while the OTIPS derivatives led to the trans isomers. After straightforward functional group transformations, the removal of the sulfonyl group at C(8) either by Julia reaction or by basic elimination (depending on the substrate used) afforded the key C(7)C(8) unsaturated indolizidines 10, 22, 30, and 31, whose stereoselective dihydroxylations with OsO4 gave a variety of cis C(1)C(8a) and-trans C(1)C(8a) trihydroxylated and tetrahydroxylated indolizidines, among which (+/-)-1,7-di-epi-castanospermine and (+/-)-1,8-di-epi-castanospermine have been reported for the first time.