benzyl (3aS,6S,7aR)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(hydroxymethyl)perhydrooxazolo<4,5-c>pyridine-5-carboxylate | 169218-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (3aS,6S,7aR)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(hydroxymethyl)perhydrooxazolo<4,5-c>pyridine-5-carboxylate
• 英文别名: 5-O-benzyl 3-O-tert-butyl (3aS,6S,7aR)-6-(hydroxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]oxazolo[4,5-c]pyridine-3,5-dicarboxylate
• CAS: 169218-63-7
• 化学式: C₂₂H₃₂N₂O₆
• 分子量: 420.506
• InChiKey: VJVFGPSUFADPHO-OKZBNKHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  88.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl (3aS,6S,7aR)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(hydroxymethyl)perhydrooxazolo<4,5-c>pyridine-5-carboxylate 在 吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 (2S,4R,5S)-4-Acetoxy-2-acetoxymethyl-5-tert-butoxycarbonylamino-piperidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Pseudodistomin C, a new piperidine alkaloid with unusual absolute configuration from the Okinawan tunicate Pseudodistoma kanoko

  摘要：

  Pseudodistomin C, a new cytotoxic piperidine alkaloid, was isolated from the Okinawan tunicate Pseudodistoma kanoko and the structure elucidated by spectral data, chemical degradations, and synthesis. The absolute configurations of the C-4 and C-5 chiral centers of pseudodistomin C were revealed by chiral HPLC analysis to be 4S and 5R, which were opposite to those of pseudodistomins A and B, previously isolated from the same tunicate, having the same planar structure as to the piperidine nucleus.

  DOI：

  10.1021/jo00126a053
• 作为产物：
  描述：

  benzyl (3aS,6S,7aR)-6-<(bromomercurio)methyl>-3-(tert-butoxycarbonyl)-2,2-dimethylperhydrooxazolo<4,5-c>pyridine-5-carboxylate 在 sodium tetrahydroborate 、 氧气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以85%的产率得到benzyl (3aS,6S,7aR)-3-(tert-butoxycarbonyl)-2,2-dimethyl-6-(hydroxymethyl)perhydrooxazolo<4,5-c>pyridine-5-carboxylate
  参考文献：
  名称：

  Pseudodistomin C, a new piperidine alkaloid with unusual absolute configuration from the Okinawan tunicate Pseudodistoma kanoko

  摘要：

  Pseudodistomin C, a new cytotoxic piperidine alkaloid, was isolated from the Okinawan tunicate Pseudodistoma kanoko and the structure elucidated by spectral data, chemical degradations, and synthesis. The absolute configurations of the C-4 and C-5 chiral centers of pseudodistomin C were revealed by chiral HPLC analysis to be 4S and 5R, which were opposite to those of pseudodistomins A and B, previously isolated from the same tunicate, having the same planar structure as to the piperidine nucleus.

  DOI：

  10.1021/jo00126a053