(3aS,7R,8aR,8bR)-7-hydroxy-2,2-dimethylhexahydro-6H-[1,3]dioxolo[4,5-a]pyrrolizin-6-one | 1060658-02-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯里西啶类
• 英文名称: (3aS,7R,8aR,8bR)-7-hydroxy-2,2-dimethylhexahydro-6H-[1,3]dioxolo[4,5-a]pyrrolizin-6-one
• CAS: 1060658-02-7
• 化学式: C₁₀H₁₅NO₄
• 分子量: 213.233
• InChiKey: MRODLZRYNRLCQK-OOJXKGFFSA-N

反应信息

• 作为反应物：
  描述：

  (3aS,7R,8aR,8bR)-7-hydroxy-2,2-dimethylhexahydro-6H-[1,3]dioxolo[4,5-a]pyrrolizin-6-one 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到(3aS,7R,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
• 作为产物：
  描述：

  (3R,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 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到(3aS,7R,8aR,8bR)-7-hydroxy-2,2-dimethylhexahydro-6H-[1,3]dioxolo[4,5-a]pyrrolizin-6-one
  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