9-[(3aR,4R,6R,6aR)-6-[bis(phenylsulfanyl)phosphoryloxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1-[(3aS,4R,6R,6aR)-6-(dianilinophosphoryloxymethyl)-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-8-bromopurin-6-one | 239080-31-0

• 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: 9-[(3aR,4R,6R,6aR)-6-[bis(phenylsulfanyl)phosphoryloxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1-[(3aS,4R,6R,6aR)-6-(dianilinophosphoryloxymethyl)-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-8-bromopurin-6-one
• CAS: 239080-31-0
• 化学式: C₄₆H₄₉BrN₆O₁₀P₂S₂
• 分子量: 1051.91
• InChiKey: QJQYJLLKBVGBAJ-LDRSYFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  67
• 可旋转键数：
  16
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  224
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  9-[(3aR,4R,6R,6aR)-6-[bis(phenylsulfanyl)phosphoryloxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1-[(3aS,4R,6R,6aR)-6-(dianilinophosphoryloxymethyl)-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-8-bromopurin-6-one 在 亚硝酸异戊酯 、 亚膦酸 、 三乙胺 作用下， 以 吡啶 、 乙酸酐 、 溶剂黄146 为溶剂， 以88%的产率得到8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(phosphoryl)oxy]methyl]cyclopentyl]-5'-O-[(phenylthio)phosphoryl]-2',3'-O-isopropylideneinosine triethylammonium salt
  参考文献：
  名称：

  Alternative synthesis of cyclic IDP-carbocyclic ribose. Efficient cyclization of an 8-bromo-N1-[5-(phosphoryl)carbocyclic-ribosyl]inosine 5′-phenylthiophosphate derivative mediated by iodine

  摘要：

  An efficient synthesis of cyclic IDP-carbocyclic-ribose, as a stable mimic for cyclic ADP-ribose, was achieved. N-1-Carbocyclic-ribosylinosine derivative 15, prepared from N-1-(2,4-dinitrophenyl)inosine derivative 10 and an optically active carbocyclic amine 11, was converted to 8-bromo-N-1-carbocyclic-ribosylinosine bis-phosphate derivative 20. Treatment of 20 with I-2 in the presence of molecular sieves in pyridine gave the desired cyclic product 8 quantitatively, which was deprotected and reductively debrominated to give the target cyclic IDP-carbocyclic ribose (3). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00977-6
• 作为产物：
  描述：

  N,N'-二苯基磷酰氯二胺 在 吡啶 、 四氮唑 、 三苯基氯硅烷 、 溶剂黄146 作用下， 生成 9-[(3aR,4R,6R,6aR)-6-[bis(phenylsulfanyl)phosphoryloxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1-[(3aS,4R,6R,6aR)-6-(dianilinophosphoryloxymethyl)-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-8-bromopurin-6-one
  参考文献：
  名称：

  Alternative synthesis of cyclic IDP-carbocyclic ribose. Efficient cyclization of an 8-bromo-N1-[5-(phosphoryl)carbocyclic-ribosyl]inosine 5′-phenylthiophosphate derivative mediated by iodine

  摘要：

  An efficient synthesis of cyclic IDP-carbocyclic-ribose, as a stable mimic for cyclic ADP-ribose, was achieved. N-1-Carbocyclic-ribosylinosine derivative 15, prepared from N-1-(2,4-dinitrophenyl)inosine derivative 10 and an optically active carbocyclic amine 11, was converted to 8-bromo-N-1-carbocyclic-ribosylinosine bis-phosphate derivative 20. Treatment of 20 with I-2 in the presence of molecular sieves in pyridine gave the desired cyclic product 8 quantitatively, which was deprotected and reductively debrominated to give the target cyclic IDP-carbocyclic ribose (3). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00977-6