5-acetamido-2-isopropoxy-6-(1,2,3-trihydroxypropyl)-5,6-dihydro-2H-pyran-2-carboxylic acid | 1562663-88-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetamido-2-isopropoxy-6-(1,2,3-trihydroxypropyl)-5,6-dihydro-2H-pyran-2-carboxylic acid
• 英文别名: (2R,3R,6S)-3-acetamido-6-propan-2-yloxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-2,3-dihydropyran-6-carboxylic acid
• CAS: 1562663-88-0
• 化学式: C₁₄H₂₃NO₈
• 分子量: 333.339
• InChiKey: NQCKPHTYTDMBIF-SKENRDBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 IR-120 (H⁺ form) resin 作用下， 以 甲醇 、 水 为溶剂， 反应 15.0h， 以34%的产率得到
  参考文献：
  名称：

  Ferrier Glycosylation Reaction Catalyzed by Bi(OTf)3-Montmorillonite K-10: Efficient Synthesis of 3,4-Unsaturated Sialic Acid Derivatives: Synthesis and Biological Evaluation as Inhibitors of Human Parainfluenza Virus Type 1

  摘要：

  The reaction of the 4,5-oxazoline derivative of sialic acid with various alcohols was effectively promoted by a catalytic amount of montmorillonite K-10 clay-supported Bi(OTf)(3) to produce a variety of 3,4-unsaturated sialic acids via the Ferrier glycosylation reaction in moderate yields. The deprotection of the isopropylidene group and hydrolysis of the ester group of 7a-g gave 4a-f, whose inhibitory activities against hPIV-1 sialidase were studied.

  DOI：

  10.3987/com-13-12861