(3aS,7S,8aR,8bR)-2,2-dimethylhexahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizin-7-ol | 1060658-05-0

• 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,7S,8aR,8bR)-2,2-dimethylhexahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizin-7-ol
• 英文别名: (3aS,7S,8aR,8bR)-2,2-dimethyl-4,6,7,8,8a,8b-hexahydro-3aH-[1,3]dioxolo[4,5-a]pyrrolizin-7-ol
• CAS: 1060658-05-0
• 化学式: C₁₀H₁₇NO₃
• 分子量: 199.25
• InChiKey: SLOHQHUDELBKNC-UYXSQOIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aS,7S,8aR,8bR)-2,2-dimethylhexahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizin-7-ol 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以90%的产率得到(1R,2S,6S,7aR)-hexahydro-1H-pyrrolizine-1,2,6-triol
  参考文献：
  名称：

  A convenient synthesis of new enantiomerically pure trihydroxypyrrolizidines using l-erythrose glycosylhydroxylamine as a masked acyclic chiral nitrone

  摘要：

  A route has been developed for the synthesis of enantiomerically pure trihydroxylated pyrrolizidines starting from L-erythrose glycosylhydroxylamine. The latter acts as a masked acyclic nitrone and reacts diastereoselectively from its Re-face with methyl acrylate to give the corresponding isoxazolidines, which after reductive N-O cleavage are recyclized to trihydroxypyrrolizidines via a Mitsunobu condensation. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.093
• 作为产物：
  描述：

  (3S,5R)-3-hydroxy-5-[(4'R,5'S)-5'-(hydroxymethyl)-2,2'-dimethyl-1',3'-dioxolan-4'-yl]-2-pyrrolidone 在 三丁基膦 、 1,1'-azodicarbonyl-dipiperidine 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 以68%的产率得到(3aS,7S,8aR,8bR)-2,2-dimethylhexahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizin-7-ol
  参考文献：
  名称：

  A convenient synthesis of new enantiomerically pure trihydroxypyrrolizidines using l-erythrose glycosylhydroxylamine as a masked acyclic chiral nitrone

  摘要：

  A route has been developed for the synthesis of enantiomerically pure trihydroxylated pyrrolizidines starting from L-erythrose glycosylhydroxylamine. The latter acts as a masked acyclic nitrone and reacts diastereoselectively from its Re-face with methyl acrylate to give the corresponding isoxazolidines, which after reductive N-O cleavage are recyclized to trihydroxypyrrolizidines via a Mitsunobu condensation. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.093