tert-butyl (3aR,4R,7R,7aS)-4-azido-7-(2,2-dimethylpropanoyloxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyridine-5-carboxylate | 319911-77-8

• 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: tert-butyl (3aR,4R,7R,7aS)-4-azido-7-(2,2-dimethylpropanoyloxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyridine-5-carboxylate
• CAS: 319911-77-8
• 化学式: C₁₉H₃₂N₄O₆
• 分子量: 412.486
• InChiKey: UWGZRRFKQPNKEI-RFGFWPKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl (3aR,4R,7R,7aS)-4-azido-7-(2,2-dimethylpropanoyloxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyridine-5-carboxylate 在 palladium on activated charcoal 吡啶 、 四丁基氢氧化铵 、 氢气 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 41.0h， 生成 (2S,3R,4S,5R)-N-(tert-butoxycarbonyl)-5-hydroxymethyl-3,4-O-isopropylidene-2-(trifluoroacetamido)-3,4-piperidinediol
  参考文献：
  名称：

  Synthesis of the Sialidase Inhibitor Siastatin B

  摘要：

  The resolved piperidinecarboxylate (R)-7 was converted to siastatin B (1) by an efficient and stereoselective sequence that includes a bromo-beta -lactonization and an N-acyliminium azidation. Two analogues (3 and 4) of siastatin were also prepared.

  DOI：

  10.1021/ol0066680
• 作为产物：
  描述：

  1-N-(t-butoxycarbonyl)-(4R)-hydroxy-(3S)-(pivaloyloxymethyl)-1,2,3,4-tetrahydropyridine 在 叠氮基三甲基硅烷 、 三氟化硼乙醚 、 碳酸氢钠 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 生成 tert-butyl (3aR,4R,7R,7aS)-4-azido-7-(2,2-dimethylpropanoyloxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyridine-5-carboxylate
  参考文献：
  名称：

  Synthesis of the Sialidase Inhibitor Siastatin B

  摘要：

  The resolved piperidinecarboxylate (R)-7 was converted to siastatin B (1) by an efficient and stereoselective sequence that includes a bromo-beta -lactonization and an N-acyliminium azidation. Two analogues (3 and 4) of siastatin were also prepared.

  DOI：

  10.1021/ol0066680

文献信息

• Synthesis of the Sialidase Inhibitor Siastatin B
  作者：Spencer Knapp、Dalian Zhao

  DOI：10.1021/ol0066680

  日期：2000.12.1

  The resolved piperidinecarboxylate (R)-7 was converted to siastatin B (1) by an efficient and stereoselective sequence that includes a bromo-beta -lactonization and an N-acyliminium azidation. Two analogues (3 and 4) of siastatin were also prepared.