(3R,4R)-1-tert-butoxycarbonyl-3-acetoxy-4-chloropiperidine | 951766-69-1

• 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: (3R,4R)-1-tert-butoxycarbonyl-3-acetoxy-4-chloropiperidine
• 英文别名: tert-butyl (3R,4R)-3-acetyloxy-4-chloropiperidine-1-carboxylate
• CAS: 951766-69-1
• 化学式: C₁₂H₂₀ClNO₄
• 分子量: 277.748
• InChiKey: JXHZJLVYGVKZFM-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (3R,4R)-1-tert-butoxycarbonyl-3-acetoxy-4-chloropiperidine 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以88%的产率得到(3R,4S)-1-tert-butoxycarbonyl-3,4-epoxypiperidine
  参考文献：
  名称：

  2-Deoxyribose as a Rich Source of Chiral 5-Carbon Building Blocks

  摘要：

  [GRAPHICS]We have developed concise routes to a number of useful chiral 5-carbon synthetic building blocks using readily available: 0-1-methyl-2-deoxyribose as starting material. Novel transformations include the use of indium triflate to catalyze the oxidation of a methyl furanoside to the corresponding lactone with MCPBA and the Vasella-type fragmentation of a 5-iodo furanoside using chromium(II) chloride when zinc proved ineffective. In addition, 3,4-disubstitued piperidine derivatives were prepared without hydroxyl group protection via a simple reductive amination reaction.

  DOI：

  10.1021/jo0712143
• 作为产物：
  描述：

  5-azido-2,5-dideoxy-D-erythro-pentofuranose 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、413.7 kPa 条件下， 反应 73.0h， 生成 (3R,4R)-1-tert-butoxycarbonyl-3-acetoxy-4-chloropiperidine
  参考文献：
  名称：

  2-Deoxyribose as a Rich Source of Chiral 5-Carbon Building Blocks

  摘要：

  [GRAPHICS]We have developed concise routes to a number of useful chiral 5-carbon synthetic building blocks using readily available: 0-1-methyl-2-deoxyribose as starting material. Novel transformations include the use of indium triflate to catalyze the oxidation of a methyl furanoside to the corresponding lactone with MCPBA and the Vasella-type fragmentation of a 5-iodo furanoside using chromium(II) chloride when zinc proved ineffective. In addition, 3,4-disubstitued piperidine derivatives were prepared without hydroxyl group protection via a simple reductive amination reaction.

  DOI：

  10.1021/jo0712143