1-((2R,3R,4R,5S)-4-{2-[(2S,3S,4R,5R)-5-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-4-methoxy-tetrahydro-furan-2-ylmethylsulfanyl]-ethyl}-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione | 171671-96-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 1-((2R,3R,4R,5S)-4-{2-[(2S,3S,4R,5R)-5-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-4-methoxy-tetrahydro-furan-2-ylmethylsulfanyl]-ethyl}-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
• CAS: 171671-96-8
• 化学式: C₂₃H₃₂N₄O₁₀S
• 分子量: 556.594
• InChiKey: XEGALQIPBSBFHU-LDPALMAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.69
• 重原子数：
  38.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  187.1
• 氢给体数：
  4.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  1-((2R,3R,4R,5S)-4-{2-[(2S,3S,4R,5R)-5-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-4-methoxy-tetrahydro-furan-2-ylmethylsulfanyl]-ethyl}-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 在 三乙胺 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Synthesis of 2′-Substituted Sulfide-Linked Dinucleotides

  摘要：

  3'-Deoxy-3'-(2-mesyloxyethyl)ribofuranosylthymine derivative 3, and its 2'-methoxy (16) and 2'-deoxy (38) analogs were condensed with 5'-deoxy-5'-thiothymidine 4 and 17 or 2'-O-methyl-5'-deoxy-5'-thiouridine 34 and 37 to provide, after standard functional group transformations, thymidine-thymidine and uridine-thymidine dimers 9, 21, 43 and 47. Oxidation of model sulfide dimer 48 with oxone gave sulfone 49. It was not stable to 27% ammonia.

  DOI：

  10.1080/15257779508010717
• 作为产物：
  描述：

  1-[(2R,3R,4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(2-hydroxy-ethyl)-3-methoxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1-((2R,3R,4R,5S)-4-{2-[(2S,3S,4R,5R)-5-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-4-methoxy-tetrahydro-furan-2-ylmethylsulfanyl]-ethyl}-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of 2′-Substituted Sulfide-Linked Dinucleotides

  摘要：

  3'-Deoxy-3'-(2-mesyloxyethyl)ribofuranosylthymine derivative 3, and its 2'-methoxy (16) and 2'-deoxy (38) analogs were condensed with 5'-deoxy-5'-thiothymidine 4 and 17 or 2'-O-methyl-5'-deoxy-5'-thiouridine 34 and 37 to provide, after standard functional group transformations, thymidine-thymidine and uridine-thymidine dimers 9, 21, 43 and 47. Oxidation of model sulfide dimer 48 with oxone gave sulfone 49. It was not stable to 27% ammonia.

  DOI：

  10.1080/15257779508010717