(5S,6S)-5-benzyloxy-1-(tert-butyloxycarbonyl)-6-methyl-2-piperidinone | 1175565-49-7

• 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: (5S,6S)-5-benzyloxy-1-(tert-butyloxycarbonyl)-6-methyl-2-piperidinone
• 英文别名: tert-butyl (2S,3S)-2-methyl-6-oxo-3-phenylmethoxypiperidine-1-carboxylate
• CAS: 1175565-49-7
• 化学式: C₁₈H₂₅NO₄
• 分子量: 319.401
• InChiKey: LSNFEZJHCIEHAL-ZFWWWQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S,6S)-5-benzyloxy-1-(tert-butyloxycarbonyl)-6-methyl-2-piperidinone 、 6-(tert-butyldimethylsilanyloxy)-1-hexylmagnesium bromide 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.67h， 以68%的产率得到tert-butyl [(2S,3S)-3-benzyloxy-12-(tert-butyldimethylsilyloxy)-6-oxododecan-2-yl]carbamate
  参考文献：
  名称：

  An enantioselective synthesis of (+)-azimic acid

  摘要：

  Herein we report a concise enantioselective synthesis of (+)-azimic acid starting from (5S,6S)-6-methyl-5-benzyloxy-2-piperidinone 8a, which was prepared from protected (S)-3-hydroxyglutarimide 6 according to a method recently disclosed in our laboratory. The key step is a stepwise regioselective reductive alkylation of the imide 10, which established the 2,6-cis-stereochemistry in excellent diastereoselectivity. (C) 2009 Elsevier Ltd. All Fights reserved.

  DOI：

  10.1016/j.tetasy.2009.04.008
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (5S,6S)-5-benzyloxy-6-methyl-2-piperidinone 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到(5S,6S)-5-benzyloxy-1-(tert-butyloxycarbonyl)-6-methyl-2-piperidinone
  参考文献：
  名称：

  An enantioselective synthesis of (+)-azimic acid

  摘要：

  Herein we report a concise enantioselective synthesis of (+)-azimic acid starting from (5S,6S)-6-methyl-5-benzyloxy-2-piperidinone 8a, which was prepared from protected (S)-3-hydroxyglutarimide 6 according to a method recently disclosed in our laboratory. The key step is a stepwise regioselective reductive alkylation of the imide 10, which established the 2,6-cis-stereochemistry in excellent diastereoselectivity. (C) 2009 Elsevier Ltd. All Fights reserved.

  DOI：

  10.1016/j.tetasy.2009.04.008

文献信息

• An enantioselective synthesis of (+)-azimic acid
  作者：Kai-Jiong Xiao、Liang-Xian Liu、Pei-Qiang Huang

  DOI：10.1016/j.tetasy.2009.04.008

  日期：2009.6

  Herein we report a concise enantioselective synthesis of (+)-azimic acid starting from (5S,6S)-6-methyl-5-benzyloxy-2-piperidinone 8a, which was prepared from protected (S)-3-hydroxyglutarimide 6 according to a method recently disclosed in our laboratory. The key step is a stepwise regioselective reductive alkylation of the imide 10, which established the 2,6-cis-stereochemistry in excellent diastereoselectivity. (C) 2009 Elsevier Ltd. All Fights reserved.