(3R,5R,6S)-ethyl 1-benzyl-3-hydroxy-6-methyl-2-oxo-5-(pivaloyloxy)piperidine-3-carboxylate | 1224514-79-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3R,5R,6S)-ethyl 1-benzyl-3-hydroxy-6-methyl-2-oxo-5-(pivaloyloxy)piperidine-3-carboxylate
• 英文别名: ethyl (3R,5R,6S)-1-benzyl-5-(2,2-dimethylpropanoyloxy)-3-hydroxy-6-methyl-2-oxopiperidine-3-carboxylate
• CAS: 1224514-79-7
• 化学式: C₂₁H₂₉NO₆
• 分子量: 391.464
• InChiKey: AWZAFRGTUSCBPX-CMPZQBNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,5R,6S)-ethyl 1-benzyl-3-hydroxy-6-methyl-2-oxo-5-(pivaloyloxy)piperidine-3-carboxylate 在 sodium ethanolate 、 盐酸 作用下， 以 乙醇 为溶剂， 反应 15.0h， 以48%的产率得到(1R,4S,5R)-3-benzyl-1-hydroxy-4-methyl-6-oxa-3-azabicyclo[3.2.1]octane-2,7-dione
  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
• 作为产物：
  描述：

  (5R,6S)-ethyl 1-benzyl-6-methyl-2-oxo-5-(pivaloyloxy)piperidine-3-carboxylate 在 正丁基锂 、 二异丙胺 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.91h， 以83%的产率得到(3R,5R,6S)-ethyl 1-benzyl-3-hydroxy-6-methyl-2-oxo-5-(pivaloyloxy)piperidine-3-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