{[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy]-hydroxy-phosphorylmethyl}-phosphonic acid mono-((3aR,4R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl) ester | 189275-81-8

• 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: {[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy]-hydroxy-phosphorylmethyl}-phosphonic acid mono-((3aR,4R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl) ester
• 英文别名: [(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy-[[[(3aR,4R,6R,6aR)-2,2-dimethyl-4-phenylmethoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy-hydroxyphosphoryl]methyl]phosphinic acid
• CAS: 189275-81-8
• 化学式: C₂₉H₃₉N₅O₁₃P₂
• 分子量: 727.602
• InChiKey: CGQBJFYNGGACNE-NUGCJFILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  49
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  227
• 氢给体数：
  3
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  {[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy]-hydroxy-phosphorylmethyl}-phosphonic acid mono-((3aR,4R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl) ester 在 Dowex 50 、 氢气 作用下， 生成 P₁-(adenosin-5'-yl)-P₂-(D-ribose-5-yl)methylenebis(phosphonic acid) 、 P1-(adenosin-5'-yl)-P2-(D-ribose-5-yl)methylenebis(phosphonic acid)
  参考文献：
  名称：

  Efficient Synthesis of Methylenebis(phosphonate) Analogues of P¹,P²-Disubstituted Pyrophosphates of Biological Interest. A Novel Plausible Mechanism

  摘要：

  Synthesis of novel nucleoside bicyclic trisanhydrides 7 in the reaction of nucleoside-5'-methylenebis-(phosphonate)s (4) with DCC is described. They were obtained by P-1,P-3- and P-2,P-3-dehydration of initially formed P-1,P-2,P-3,P-4-bismethylenetetraphosphonate 6. Reaction of 7 (N = 2',3'-O-isopropylideneadenosin-5'-yl) with 2',3'-O-isopropylidenetiazofurin gave, after hydrolysis and deisopropylidenation, beta-methylene-TAD (10a), the known potent inhibitor of inosine monophosphate dehydrogenase (IMPDH). Similar reaction of 7 with benzyl 2,3-O-isopropylidene-beta-D-riboside followed by hydrolysis and deprotection afforded a new methylenebis(phosphonate) analogue of ADP-ribose 10b. Upon reaction of 7 with riboflavin, the corresponding beta-methylene-FAD (10c) was obtained. Bicyclic trisanhydride 7 prepared from (2',3'-O-isopropylidene-N-4-acetylcytidin-5'yl)methylenebis(phosphonate) was used in the synthesis of the methylenebis(phosphonate) analogues of CDP-ethanolamine 10d and CDP-dipalmitoylglycerol 10e.

  DOI：

  10.1021/ja964058i
• 作为产物：
  描述：

  P¹,P²,P³,P⁴-bismethylene-P¹,P⁴-di(2',3'-O-isopropylideneadenosine) tetraphosphonate 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二甲基亚砜 为溶剂， 生成 {[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy]-hydroxy-phosphorylmethyl}-phosphonic acid mono-((3aR,4R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl) ester
  参考文献：
  名称：

  Efficient Synthesis of Methylenebis(phosphonate) Analogues of P¹,P²-Disubstituted Pyrophosphates of Biological Interest. A Novel Plausible Mechanism

  摘要：

  Synthesis of novel nucleoside bicyclic trisanhydrides 7 in the reaction of nucleoside-5'-methylenebis-(phosphonate)s (4) with DCC is described. They were obtained by P-1,P-3- and P-2,P-3-dehydration of initially formed P-1,P-2,P-3,P-4-bismethylenetetraphosphonate 6. Reaction of 7 (N = 2',3'-O-isopropylideneadenosin-5'-yl) with 2',3'-O-isopropylidenetiazofurin gave, after hydrolysis and deisopropylidenation, beta-methylene-TAD (10a), the known potent inhibitor of inosine monophosphate dehydrogenase (IMPDH). Similar reaction of 7 with benzyl 2,3-O-isopropylidene-beta-D-riboside followed by hydrolysis and deprotection afforded a new methylenebis(phosphonate) analogue of ADP-ribose 10b. Upon reaction of 7 with riboflavin, the corresponding beta-methylene-FAD (10c) was obtained. Bicyclic trisanhydride 7 prepared from (2',3'-O-isopropylidene-N-4-acetylcytidin-5'yl)methylenebis(phosphonate) was used in the synthesis of the methylenebis(phosphonate) analogues of CDP-ethanolamine 10d and CDP-dipalmitoylglycerol 10e.

  DOI：

  10.1021/ja964058i