cis-((5-((4-amino-2-oxopyrimidin-1(2H)-yl)methyl)-1,3-oxathiolan-2-yl)methyl) (2R,3S,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl phenyl phosphate | 1260213-84-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: cis-((5-((4-amino-2-oxopyrimidin-1(2H)-yl)methyl)-1,3-oxathiolan-2-yl)methyl) (2R,3S,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl phenyl phosphate
• CAS: 1260213-84-0
• 化学式: C₃₁H₄₄N₅O₁₀PSSi
• 分子量: 737.843
• InChiKey: DAZAXQJRIFKLQP-NYUNQEPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  49.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  188.22
• 氢给体数：
  2.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  cis-((5-((4-amino-2-oxopyrimidin-1(2H)-yl)methyl)-1,3-oxathiolan-2-yl)methyl) (2R,3S,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl phenyl phosphate 在 盐酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.0h， 以85%的产率得到cis-((5-((4-amino-2-oxopyrimidin-1(2H)-yl)methyl)-1,3-oxathiolan-2-yl)methyl) (2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl phenyl phosphate
  参考文献：
  名称：

  Design and synthesis of novel dinucleotide analogs

  摘要：

  Syntheses of dinucleotide analogs, (S,R) cis-(4-((4-amino-2-oxopyrimidin-1(2H)-yl)methyl)-1,3-dioxolan-2-yl)methyl (2R,3R,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl hydrogen phosphate (5a) and (S,R) cis-(5-((4-amino-2-oxopyrimidin-1(2H)-yl)methyl)-1,3-oxathiolan-2-yl)methyl (2R,3R,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl hydrogen phosphate (5b), were accomplished by the use of a new strategy. The use of phenyldichlorophosphate (Method A) as the coupling reagent was shown to possess superiority relative to the reported use of di(1H-benzo[d][1,2,3]triazol-1-yl)phenyl phosphonate (Method B).

  DOI：

  10.1007/bf03246046
• 作为产物：
  描述：

  二氯磷酸苯酯 、 5’-O-(叔丁基二甲基甲硅烷基)胸苷 、 L-homolamivudine 在 吡啶 、 1-羟基苯并三唑 、 N-甲基咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以46%的产率得到cis-((5-((4-amino-2-oxopyrimidin-1(2H)-yl)methyl)-1,3-oxathiolan-2-yl)methyl) (2R,3S,5R)-2-((tert-butyldimethylsilyloxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl phenyl phosphate
  参考文献：
  名称：

  Design and synthesis of novel dinucleotide analogs

  摘要：

  Syntheses of dinucleotide analogs, (S,R) cis-(4-((4-amino-2-oxopyrimidin-1(2H)-yl)methyl)-1,3-dioxolan-2-yl)methyl (2R,3R,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl hydrogen phosphate (5a) and (S,R) cis-(5-((4-amino-2-oxopyrimidin-1(2H)-yl)methyl)-1,3-oxathiolan-2-yl)methyl (2R,3R,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl hydrogen phosphate (5b), were accomplished by the use of a new strategy. The use of phenyldichlorophosphate (Method A) as the coupling reagent was shown to possess superiority relative to the reported use of di(1H-benzo[d][1,2,3]triazol-1-yl)phenyl phosphonate (Method B).

  DOI：

  10.1007/bf03246046