(1R,6R,7S,8aR)-1-tert-butyldimethylsilyloxy-6,7-(isopropylidene)dioxy-indolizidine | 334022-64-9

• 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: (1R,6R,7S,8aR)-1-tert-butyldimethylsilyloxy-6,7-(isopropylidene)dioxy-indolizidine
• 英文别名: [(3aR,8R,8aR,9aS)-2,2-dimethyl-3a,4,6,7,8,8a,9,9a-octahydro-[1,3]dioxolo[4,5-f]indolizin-8-yl]oxy-tert-butyl-dimethylsilane
• CAS: 334022-64-9
• 化学式: C₁₇H₃₃NO₃Si
• 分子量: 327.539
• InChiKey: WNOKZCRHLHFTTD-APIJFGDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,6R,7S,8aR)-1-tert-butyldimethylsilyloxy-6,7-(isopropylidene)dioxy-indolizidine 在 四丁基氟化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (1R,6R,7S,8aR)-1,6,7-trihydroxy-indolizidine
  参考文献：
  名称：

  A chiral hexahydroindolizine as key intermediate in the synthesis of tri- and tetrahydroxyindolizidines

  摘要：

  The highly stereoselective functionalization of hexahydro-3-oxo-indolizine 6 has been examined. The bishydroxylated product can be transformed successfully into the trihydroxyindolizidine 11 in 57% overall yield. in addition, a simple elimination process to give the a,P-unsaturated lactam 13 and a second highly stereoselective bishydroxylation can be used to synthesise the tetrahydroxyindolizidine 19 in 30% overall yield. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(00)01034-6
• 作为产物：
  描述：

  (1R,8aR)-1-(tert-Butyl-dimethyl-silanyloxy)-1,5,8,8a-tetrahydro-2H-indolizin-3-one 在 potassium osmate(VI) 、 dimethyl sulfide borane 、 4-甲基苯磺酸吡啶 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 4.0h， 生成 (1R,6R,7S,8aR)-1-tert-butyldimethylsilyloxy-6,7-(isopropylidene)dioxy-indolizidine
  参考文献：
  名称：

  A chiral hexahydroindolizine as key intermediate in the synthesis of tri- and tetrahydroxyindolizidines

  摘要：

  The highly stereoselective functionalization of hexahydro-3-oxo-indolizine 6 has been examined. The bishydroxylated product can be transformed successfully into the trihydroxyindolizidine 11 in 57% overall yield. in addition, a simple elimination process to give the a,P-unsaturated lactam 13 and a second highly stereoselective bishydroxylation can be used to synthesise the tetrahydroxyindolizidine 19 in 30% overall yield. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(00)01034-6

文献信息

• A chiral hexahydroindolizine as key intermediate in the synthesis of tri- and tetrahydroxyindolizidines
  作者：Michael Lennartz、Eberhard Steckhan

  DOI：10.1016/s0040-4020(00)01034-6

  日期：2001.1

  The highly stereoselective functionalization of hexahydro-3-oxo-indolizine 6 has been examined. The bishydroxylated product can be transformed successfully into the trihydroxyindolizidine 11 in 57% overall yield. in addition, a simple elimination process to give the a,P-unsaturated lactam 13 and a second highly stereoselective bishydroxylation can be used to synthesise the tetrahydroxyindolizidine 19 in 30% overall yield. (C) 2001 Published by Elsevier Science Ltd.