[(3aR,4R,6R,6aR)-4-(4-acetamido-2-oxopyrimidin-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy-[[2-acetamidoethoxy(hydroxy)phosphoryl]methyl]phosphinic acid | 189275-84-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3aR,4R,6R,6aR)-4-(4-acetamido-2-oxopyrimidin-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy-[[2-acetamidoethoxy(hydroxy)phosphoryl]methyl]phosphinic acid
• CAS: 189275-84-1
• 化学式: C₁₉H₃₀N₄O₁₂P₂
• 分子量: 568.414
• InChiKey: IYUGTWOSYSOBCP-MWQQHZPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.12
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  213.84
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  [(3aR,4R,6R,6aR)-4-(4-acetamido-2-oxopyrimidin-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy-[[2-acetamidoethoxy(hydroxy)phosphoryl]methyl]phosphinic acid 在 Dowex 50 、 氢气 作用下， 生成 {[(2R,3S,4R,5R)-5-(4-Acetylamino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphorylmethyl}-phosphonic acid mono-(2-acetylamino-ethyl) 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
• 作为产物：
  描述：

  N-乙酰乙醇胺 、 以 二甲基亚砜 为溶剂， 以83%的产率得到[(3aR,4R,6R,6aR)-4-(4-acetamido-2-oxopyrimidin-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy-[[2-acetamidoethoxy(hydroxy)phosphoryl]methyl]phosphinic 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