(1R,4S,5S,6R)-ethyl 3-benzyl-4-methyl-2-oxo-5-(pivaloyloxy)-7-oxa-3-azabicyclo[4.1.0]heptane-1-carboxylate | 1224514-85-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡咯
• 英文名称: (1R,4S,5S,6R)-ethyl 3-benzyl-4-methyl-2-oxo-5-(pivaloyloxy)-7-oxa-3-azabicyclo[4.1.0]heptane-1-carboxylate
• CAS: 1224514-85-5
• 化学式: C₂₁H₂₇NO₆
• 分子量: 389.448
• InChiKey: CBKBZEFUHXXVII-RYSHRAHSSA-N

反应信息

• 作为产物：
  描述：

  (5R,6S)-ethyl 1-benzyl-6-methyl-2-oxo-5-(pivaloyloxy)-1,2,5,6-tetrahydropyridine-3-carboxylate 在 叔丁基过氧化氢 、 正丁基锂 作用下， 以 四氢呋喃 、 癸烷 、 正己烷 为溶剂， 反应 0.42h， 以85%的产率得到(1R,4S,5S,6R)-ethyl 3-benzyl-4-methyl-2-oxo-5-(pivaloyloxy)-7-oxa-3-azabicyclo[4.1.0]heptane-1-carboxylate
  参考文献：
  名称：

  An enantioselective synthesis of the bicyclic core of the marine natural product awajanomycin

  摘要：

  A concise stereoselective synthesis of the N-benzylated bicyclic core of the marine natural product awajanomycin is described starting with naturally Occurring L-alanine. Key steps in the synthesis include a ring-closing metathesis to establish a delta-lactam ring followed by a stereoselective hydroxylation to instal the quaternary centre. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.123