8-bromo-2',3'-O-isopropylideneinosine-5'-O-phosphorodianilidate | 214784-90-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: 8-bromo-2',3'-O-isopropylideneinosine-5'-O-phosphorodianilidate
• 英文别名: 9-[(3aR,4R,6R,6aR)-6-(dianilinophosphoryloxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-8-bromo-3H-purin-6-one
• CAS: 214784-90-4
• 化学式: C₂₅H₂₆BrN₆O₆P
• 分子量: 617.396
• InChiKey: LAXSXDHRDLLJDJ-ZDXOVATRSA-N

物化性质

• 密度：
  1.740±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  141.62
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  8-bromo-2',3'-O-isopropylideneinosine-5'-O-phosphorodianilidate 在 四氮唑 、 18-冠醚-6 、 triisopropylbenzenesulfonyl chloride 、 四丁基氟化铵 、 亚膦酸 、 potassium carbonate 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 吡啶 、 乙二醇二甲醚 为溶剂， 生成 8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(phenylthiophosphoryl)oxy]methyl]cyclopentyl]-5'-O-(phosphoryl)-2',3'-O-isopropylideneinosine triethylammonium salt
  参考文献：
  名称：

  Synthetic studies of carbocyclic analogs of cyclic ADP-ribose. Formation of a cyclic dimer, a 36-membered-ring product, in the condensation reaction of an 8-bromo-N1-[5-(phenylthiophosphoryl)carbocyclic-ribosyl]inosine 5′-phosphate derivative mediated by AgNO3

  摘要：

  Formation of symmetric 36-membered-ring product 14 was observed in the synthetic study of a stable mimic of cyclic ADP-ribose (cADPR, 1), When 8-bromo-N-1-[5-(phenylthiophosphoryl)carbocyclic-ribosyl]inosine 5'-phosphate derivative 5 was treated with AgNO3 and Et3N in N-methyl-2-pyrrolidinone-HMPA (3:1), the substrate was dimerized and cyclized to give 14 in 39% yield, (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01575-5
• 作为产物：
  描述：

  N,N'-二苯基磷酰氯二胺 、 8-溴-2',3'-O-(1-甲基乙亚基)-肌苷 在 四氮唑 作用下， 以 吡啶 为溶剂， 以75%的产率得到8-bromo-2',3'-O-isopropylideneinosine-5'-O-phosphorodianilidate
  参考文献：
  名称：

  Synthetic studies of carbocyclic analogs of cyclic ADP-ribose. Formation of a cyclic dimer, a 36-membered-ring product, in the condensation reaction of an 8-bromo-N1-[5-(phenylthiophosphoryl)carbocyclic-ribosyl]inosine 5′-phosphate derivative mediated by AgNO3

  摘要：

  Formation of symmetric 36-membered-ring product 14 was observed in the synthetic study of a stable mimic of cyclic ADP-ribose (cADPR, 1), When 8-bromo-N-1-[5-(phenylthiophosphoryl)carbocyclic-ribosyl]inosine 5'-phosphate derivative 5 was treated with AgNO3 and Et3N in N-methyl-2-pyrrolidinone-HMPA (3:1), the substrate was dimerized and cyclized to give 14 in 39% yield, (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01575-5