(dimethylphosphonyl) 2-acetamido-1,2,4-trideoxy-β-L-erythro-hex-4-enopyranosiduronic acid | 1415506-69-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (dimethylphosphonyl) 2-acetamido-1,2,4-trideoxy-β-L-erythro-hex-4-enopyranosiduronic acid
• 英文别名: (2R,3S,4S)-3-acetamido-2-dimethoxyphosphoryl-4-hydroxy-3,4-dihydro-2H-pyran-6-carboxylic acid
• CAS: 1415506-69-2
• 化学式: C₁₀H₁₆NO₈P
• 分子量: 309.213
• InChiKey: DAUASIPKDBPUSD-KADJCCMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl [(dimethylphosphonyl) 2-acetamido-1,2,4-trideoxy-3-O-acetyl-β-L-erythro-hex-4-enopyranosid]uronate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 以41%的产率得到(dimethylphosphonyl) 2-acetamido-1,2,4-trideoxy-β-L-erythro-hex-4-enopyranosiduronic acid
  参考文献：
  名称：

  Uronosyl phosphonate-based sialidase inhibitor synthesis and conformational analysis

  摘要：

  With a view to development of novel sialidase inhibitors, mimetics of the natural inhibitor Neu5Ac2en have been prepared in which a phosphonate group replaces the sialic acid glycerol side chain. Different hex-4-en derivatives adopt half-chair conformations that place the glycosyl phosphonate in an equatorial position. For the alpha-L-threo-hex-4-en derivative this conformation is equivalent to that of Neu5Ac2en, and opposite to that seen for alkyl O-glycosides with the same overall stereochemistry. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.015

文献信息

• Uronosyl phosphonate-based sialidase inhibitor synthesis and conformational analysis
  作者：Beenu Bhatt、Robin J. Thomson、Mark von Itzstein

  DOI：10.1016/j.bmcl.2012.10.015

  日期：2012.12

  With a view to development of novel sialidase inhibitors, mimetics of the natural inhibitor Neu5Ac2en have been prepared in which a phosphonate group replaces the sialic acid glycerol side chain. Different hex-4-en derivatives adopt half-chair conformations that place the glycosyl phosphonate in an equatorial position. For the alpha-L-threo-hex-4-en derivative this conformation is equivalent to that of Neu5Ac2en, and opposite to that seen for alkyl O-glycosides with the same overall stereochemistry. (C) 2012 Elsevier Ltd. All rights reserved.