(3aS,4R,6aR)-tert-butyl 4-((R)-1-(tert-butyldimethylsilyloxy)-4-hydroxybutyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3aS,4R,6aR)-tert-butyl 4-((R)-1-(tert-butyldimethylsilyloxy)-4-hydroxybutyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• 英文别名: tert-butyl (3aS,4R,6aR)-4-[(1R)-1-[tert-butyl(dimethyl)silyl]oxy-4-hydroxybutyl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• 化学式: C₂₂H₄₃NO₆Si
• 分子量: 445.672
• InChiKey: VLLDTEMXMHJMEZ-ZJPYXAASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aS,4R,6aR)-tert-butyl 4-((R)-1-(tert-butyldimethylsilyloxy)-4-hydroxybutyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate 在 吡啶 、 2,6-二甲基吡啶 、 甲醇 、 草酰氯 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 45.0h， 生成 (1S,2R,8R,8aS)-octahydro-1,2,8-indolizidinetriol
  参考文献：
  名称：

  A facile synthesis of 1,4-dideoxy-1,4-imino-l-ribitol (LRB) and (−)-8a-epi-swainsonine from d-glutamic acid

  摘要：

  A facile synthesis of (-)-8a-epi-swainsonine 2 and 1,4-dideoxy-1,4-imino-L-ribitol (LRB) 4 has been achieved by using the versatile building block 3, which was available from cheap D-glutamic acid. The new forming stereogenic center in synthesis of 2 was constructed by highly selective reduction of the ketone 13 with Li(t-BuO)(3)AlH in THF (dr=95:5). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.075
• 作为产物：
  描述：

  (3aS,4S,6aR)-tert-butyl 4-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate 在 2,6-二甲基吡啶 、 sodium periodate 、 dimethyl sulfide borane 、 四丁基氟化铵 、 二异丁基氢化铝 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 42.25h， 生成 (3aS,4R,6aR)-tert-butyl 4-((R)-1-(tert-butyldimethylsilyloxy)-4-hydroxybutyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
  参考文献：
  名称：

  A facile synthesis of 1,4-dideoxy-1,4-imino-l-ribitol (LRB) and (−)-8a-epi-swainsonine from d-glutamic acid

  摘要：

  A facile synthesis of (-)-8a-epi-swainsonine 2 and 1,4-dideoxy-1,4-imino-L-ribitol (LRB) 4 has been achieved by using the versatile building block 3, which was available from cheap D-glutamic acid. The new forming stereogenic center in synthesis of 2 was constructed by highly selective reduction of the ketone 13 with Li(t-BuO)(3)AlH in THF (dr=95:5). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.075

文献信息

• A facile synthesis of 1,4-dideoxy-1,4-imino-l-ribitol (LRB) and (−)-8a-epi-swainsonine from d-glutamic acid
  作者：Xiao-Ling Wang、Wen-Feng Huang、Xin-Sheng Lei、Bang-Guo Wei、Guo-Qiang Lin

  DOI：10.1016/j.tet.2011.04.075

  日期：2011.7

  A facile synthesis of (-)-8a-epi-swainsonine 2 and 1,4-dideoxy-1,4-imino-L-ribitol (LRB) 4 has been achieved by using the versatile building block 3, which was available from cheap D-glutamic acid. The new forming stereogenic center in synthesis of 2 was constructed by highly selective reduction of the ketone 13 with Li(t-BuO)(3)AlH in THF (dr=95:5). (C) 2011 Elsevier Ltd. All rights reserved.