(1S,3S,4S,5R)-4-Acetylamino-3-methoxymethoxy-5-((1S,2R)-1,2,3-tris-methoxymethoxy-propyl)-cyclohexanecarboxylic acid tert-butyl ester | 212752-22-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3S,4S,5R)-4-Acetylamino-3-methoxymethoxy-5-((1S,2R)-1,2,3-tris-methoxymethoxy-propyl)-cyclohexanecarboxylic acid tert-butyl ester
• CAS: 212752-22-2
• 化学式: C₂₄H₄₅NO₁₁
• 分子量: 523.621
• InChiKey: XMWHKBIJUQJDJF-NALHQMNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.45
• 重原子数：
  36.0
• 可旋转键数：
  17.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  129.24
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (1S,3S,4S,5R)-4-Acetylamino-3-methoxymethoxy-5-((1S,2R)-1,2,3-tris-methoxymethoxy-propyl)-cyclohexanecarboxylic acid tert-butyl ester 在 吡啶 、 双氧水 、 lithium cyclohexylisopropylamide 作用下， 生成 (3S,4S,5R)-4-acetamido-3-hydroxy-5-[(1S,2R)-1,2,3-trihydroxypropyl]cyclohexene-1-carboxylic acid
  参考文献：
  名称：

  Carbocyclic Analogues ofN-Acetyl-2,3-didehydro-2-deoxy-D-neuraminic Acid (Neu5Ac2en, DANA): Synthesis and Inhibition of Viral and Bacterial Neuraminidases

  摘要：

  Inhibition of neuraminidases from Influenza A and Salmonella typhimurium is shown by the carbocyclic compound 2, whereas its double-bond isomer 1 hardly binds to these enzymes. The cyclohexenes 1 and 2 were prepared from N-acetyl-D-mannosamine in 18 steps in 2.6 and 1.6 % yields, respectively.

  DOI：

  10.1002/(sici)1521-3773(19980703)37:12<1732::aid-anie1732>3.0.co;2-i
• 作为产物：
  描述：

  (1S,3R,4R,5S)-4-Acetylamino-3-hydroxy-5-methoxymethoxy-3-((1R,2R)-1,2,3-tris-methoxymethoxy-propyl)-cyclohexanecarboxylic acid tert-butyl ester 在 palladium on activated charcoal 双[Α,Α-双(三氟甲基)苯甲醇合]二苯硫 、 水 、 氢气 、 溶剂黄146 作用下， 以 乙酸乙酯 为溶剂， 生成 (1S,3S,4S,5R)-4-Acetylamino-3-methoxymethoxy-5-((1S,2R)-1,2,3-tris-methoxymethoxy-propyl)-cyclohexanecarboxylic acid tert-butyl ester
  参考文献：
  名称：

  Carbocyclic Analogues ofN-Acetyl-2,3-didehydro-2-deoxy-D-neuraminic Acid (Neu5Ac2en, DANA): Synthesis and Inhibition of Viral and Bacterial Neuraminidases

  摘要：

  Inhibition of neuraminidases from Influenza A and Salmonella typhimurium is shown by the carbocyclic compound 2, whereas its double-bond isomer 1 hardly binds to these enzymes. The cyclohexenes 1 and 2 were prepared from N-acetyl-D-mannosamine in 18 steps in 2.6 and 1.6 % yields, respectively.

  DOI：

  10.1002/(sici)1521-3773(19980703)37:12<1732::aid-anie1732>3.0.co;2-i