methyl [(dimethylphosphonyl) 2-acetamido-1,2,4-trideoxy-3-O-acetyl-β-L-erythro-hex-4-enopyranosid]uronate | 1415506-68-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl [(dimethylphosphonyl) 2-acetamido-1,2,4-trideoxy-3-O-acetyl-β-L-erythro-hex-4-enopyranosid]uronate
• 英文别名: methyl (2R,3S,4S)-3-acetamido-4-acetyloxy-2-dimethoxyphosphoryl-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 1415506-68-1
• 化学式: C₁₃H₂₀NO₉P
• 分子量: 365.277
• InChiKey: QNKKQFAWTBEXFN-XHVZSJERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  methyl [(dimethylphosphonyl) 2-acetamido-3,4-di-O-acetyl-1,2-dideoxy-β-L-gulopyranosid]uronate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以74%的产率得到methyl [(dimethylphosphonyl) 2-acetamido-1,2,4-trideoxy-3-O-acetyl-β-L-erythro-hex-4-enopyranosid]uronate
  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