(3aS,6S,6aS)-tert-butyl 4-acetoxy-6-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate | 1314241-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3aS,6S,6aS)-tert-butyl 4-acetoxy-6-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• 英文别名: tert-butyl (3aS,6S,6aS)-4-acetyloxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• CAS: 1314241-29-6
• 化学式: C₂₁H₃₉NO₇Si
• 分子量: 445.629
• InChiKey: VKLVPKFHHSPRDT-RXMKTKRKSA-N

物化性质

• 沸点：
  472.0±45.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aS,6S,6aS)-tert-butyl 4-acetoxy-6-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate 在 三乙基硅烷 、 三氟化硼乙醚 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (2S,3S,4R)-N-tert-butoxycarbonyl-2-hydroxymethyl-3,4-O-isopropylidenepyrrolidine-3,4-diol
  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：

  (2S,3S,4S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dihydroxy-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 在 4-二甲氨基吡啶 、 三乙基硼氢化锂 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 13.5h， 生成 (3aS,6S,6aS)-tert-butyl 4-acetoxy-6-((tert-butyldimethylsilyloxy)methyl)-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