1-[(3aS,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-9-[(3aR,4R,6R,6aR)-6-(dianilinophosphoryloxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-8-bromopurin-6-one | 214784-92-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 1-[(3aS,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-9-[(3aR,4R,6R,6aR)-6-(dianilinophosphoryloxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-8-bromopurin-6-one
• CAS: 214784-92-6
• 化学式: C₄₀H₅₄BrN₆O₉PSi
• 分子量: 901.867
• InChiKey: IARGXOBAWHLWOU-TWRNFTQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.22
• 重原子数：
  58.0
• 可旋转键数：
  12.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  158.45
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  1-[(3aS,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-9-[(3aR,4R,6R,6aR)-6-(dianilinophosphoryloxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-8-bromopurin-6-one 在 四氮唑 、 triisopropylbenzenesulfonyl chloride 、 四丁基氟化铵 、 亚膦酸 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 吡啶 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 在 四氮唑 、 18-冠醚-6 、 potassium carbonate 作用下， 以 吡啶 、 乙二醇二甲醚 为溶剂， 生成 1-[(3aS,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-9-[(3aR,4R,6R,6aR)-6-(dianilinophosphoryloxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-8-bromopurin-6-one
  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