(1S,3S,4R,5S)-3-tetrahydropyranyl-4-di-tert-butylphosphatomethyl-1-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)bicyclo[3.1.0]hexane | 873780-52-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: (1S,3S,4R,5S)-3-tetrahydropyranyl-4-di-tert-butylphosphatomethyl-1-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)bicyclo[3.1.0]hexane
• 英文别名: ditert-butyl [(1S,2R,3S,5S)-5-(2,4-dioxopyrimidin-1-yl)-3-(oxan-2-yloxy)-2-bicyclo[3.1.0]hexanyl]methyl phosphate
• CAS: 873780-52-0
• 化学式: C₂₄H₃₉N₂O₈P
• 分子量: 514.556
• InChiKey: OZRPRMGNNVVOQD-PUNJOXLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1S,3S,4R,5S)-3-tetrahydropyranyl-4-di-tert-butylphosphatomethyl-1-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)bicyclo[3.1.0]hexane 在 N,N'-羰基二咪唑 、 三氟乙酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.0h， 生成 (1S,3S,4R,5S)-3-hydroxy-4-diphosphoroxymethyl-1-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)bicyclo[3.1.0]hexane
  参考文献：
  名称：

  Human P2Y₆ Receptor:  Molecular Modeling Leads to the Rational Design of a Novel Agonist Based on a Unique Conformational Preference

  摘要：

  Combining molecular dynamics (MD) in a hydrated phospholipid (DOPC) bilayer, a Monte Carlo search, and synthesis of locked nucleotide analogues, we discovered that the Southern conformation of the ribose is preferred for ligand recognition by the P2Y(6) receptor. 2'-Deoxy-(S)-methanocarbaUDP was found to be a full agonist of the receptor and displayed a 10-fold higher potency than that for the corresponding flexible 2'-deoxyUDP. MD results also suggested a conformational change of the second extracellular loop consequent to agonist binding.

  DOI：

  10.1021/jm050911p
• 作为产物：
  描述：

  (1S,3S,4R,5S)-3-tetrahydropyranyl-4-tert-butyldiphenylsilyloxymethyl-1-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)bicyclo[3.1.0]hexane 在 四氮唑 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.75h， 生成 (1S,3S,4R,5S)-3-tetrahydropyranyl-4-di-tert-butylphosphatomethyl-1-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)bicyclo[3.1.0]hexane
  参考文献：
  名称：

  Human P2Y₆ Receptor:  Molecular Modeling Leads to the Rational Design of a Novel Agonist Based on a Unique Conformational Preference

  摘要：

  Combining molecular dynamics (MD) in a hydrated phospholipid (DOPC) bilayer, a Monte Carlo search, and synthesis of locked nucleotide analogues, we discovered that the Southern conformation of the ribose is preferred for ligand recognition by the P2Y(6) receptor. 2'-Deoxy-(S)-methanocarbaUDP was found to be a full agonist of the receptor and displayed a 10-fold higher potency than that for the corresponding flexible 2'-deoxyUDP. MD results also suggested a conformational change of the second extracellular loop consequent to agonist binding.

  DOI：

  10.1021/jm050911p