Acetic acid (1S,5R,6S)-6-acetylamino-5-(2,3-diacetoxy-propoxy)-3-(diethoxy-phosphoryl)-cyclohex-2-enyl ester | 676540-49-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: Acetic acid (1S,5R,6S)-6-acetylamino-5-(2,3-diacetoxy-propoxy)-3-(diethoxy-phosphoryl)-cyclohex-2-enyl ester
• CAS: 676540-49-1
• 化学式: C₂₁H₃₄NO₁₁P
• 分子量: 507.475
• InChiKey: KJTHOOITQXESBI-YPHDSLMMSA-N

物化性质

• 沸点：
  637.5±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  34.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  152.76
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,5R,6S)-6-acetylamino-5-(2,3-diacetoxy-propoxy)-3-(diethoxy-phosphoryl)-cyclohex-2-enyl ester 在 ammonium hydroxide 作用下， 以 氯仿 为溶剂， 生成 [(3S,4R,5R)-4-Acetylamino-5-(2,3-dihydroxy-propoxy)-3-hydroxy-cyclohex-1-enyl]-phosphonic acid; compound with ammonia
  参考文献：
  名称：

  Synthesis and evaluation as sialidase inhibitors of xylo-configured cyclohexenephosphonates carrying glycerol side-chain mimics

  摘要：

  Based on a strategy previously reported by us, we have synthesized D-xylo configured cyclohexenephosphonates designed to mimic the transition state of the sialidase reaction. The double bond orientation corresponds to the benchmark inhibitor Neu5Ac2en and we could selectively introduce hydroxyalkyl substituents in order to simulate the glycerol side-chain of neuraminic acid. The inhibitory activity of a set of compounds towards bacterial sialidases was tested and interesting differences in activity were found. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.003
• 作为产物：
  描述：

  diethyl (3S,4S,5R)-4-azido-5-(prop-2'-enyloxy)-3-triisopropylsilyloxy-1-cyclohexene-1-phosphonate 在 吡啶 、 四氧化锇 、 N-甲基吲哚酮 、 硫化氢 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 Acetic acid (1S,5R,6S)-6-acetylamino-5-(2,3-diacetoxy-propoxy)-3-(diethoxy-phosphoryl)-cyclohex-2-enyl ester
  参考文献：
  名称：

  Synthesis and evaluation as sialidase inhibitors of xylo-configured cyclohexenephosphonates carrying glycerol side-chain mimics

  摘要：

  Based on a strategy previously reported by us, we have synthesized D-xylo configured cyclohexenephosphonates designed to mimic the transition state of the sialidase reaction. The double bond orientation corresponds to the benchmark inhibitor Neu5Ac2en and we could selectively introduce hydroxyalkyl substituents in order to simulate the glycerol side-chain of neuraminic acid. The inhibitory activity of a set of compounds towards bacterial sialidases was tested and interesting differences in activity were found. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.003