bis(5'-adenosyl) thiophosphate

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: bis(5'-adenosyl) thiophosphate
• 英文别名: (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxymethyl]oxolane-3,4-diol
• 化学式: C₂₀H₂₅N₁₀O₉PS
• 分子量: 612.52
• InChiKey: WJKPULLQTIBXJQ-XPWFQUROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  309
• 氢给体数：
  7
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  腺苷 在 四氮唑 、 2-(N,N-diisopropylamino)-2-oxo-1,3,2-oxathiaphospholane 、 苯基二硫化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二甲基亚砜 、 乙腈 为溶剂， 反应 40.0h， 以67%的产率得到bis(5'-adenosyl) thiophosphate
  参考文献：
  名称：

  Solid-Phase Synthesis of Dinucleoside and Nucleoside-Carbohydrate Phosphodiesters and Thiophosphodiesters

  摘要：

  Unprotected nucleosides (ROH) were reacted with two polymers bound to N, N-diisopropylamino- 1,3,2-oxathiaphospholane in the presence of 1H-terazole. Oxidation with tertbutyl hydroperoxide or sulfurization with Beaucage's reagent, followed by the 1,3,2-oxathiaphospholane ring opening with unprotected nucleosides or carbohydrates (R'OH) in the presence of DBU, afforded nucleoside-(5'-5')-nucleoside or nucleoside- carbohydrate phosphodiester and thiophosphodiester derivatives through the elimination of polymer-bound ethylene episulfide. This strategy offers the advantages of facile isolation of final products and monosubstitution of unprotected nucleosides and carbohydrates.

  DOI：

  10.1021/jo0611115

文献信息

• Solid-Phase Synthesis of Dinucleoside and Nucleoside-Carbohydrate Phosphodiesters and Thiophosphodiesters
  作者：Yousef Ahmadibeni、Keykavous Parang

  DOI：10.1021/jo0611115

  日期：2006.8.1

  Unprotected nucleosides (ROH) were reacted with two polymers bound to N, N-diisopropylamino- 1,3,2-oxathiaphospholane in the presence of 1H-terazole. Oxidation with tertbutyl hydroperoxide or sulfurization with Beaucage's reagent, followed by the 1,3,2-oxathiaphospholane ring opening with unprotected nucleosides or carbohydrates (R'OH) in the presence of DBU, afforded nucleoside-(5'-5')-nucleoside or nucleoside- carbohydrate phosphodiester and thiophosphodiester derivatives through the elimination of polymer-bound ethylene episulfide. This strategy offers the advantages of facile isolation of final products and monosubstitution of unprotected nucleosides and carbohydrates.