3'-deoxythymidin-3'-ylsulfamoyl-[3'(N)->5'(O)]-3'-O-acetylthymidine | 919367-38-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3'-deoxythymidin-3'-ylsulfamoyl-[3'(N)->5'(O)]-3'-O-acetylthymidine
• 英文别名: [(2R,3S,5R)-2-[[(2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]sulfamoyloxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
• CAS: 919367-38-7
• 化学式: C₂₂H₂₉N₅O₁₂S
• 分子量: 587.565
• InChiKey: WCUOPWUYDPQVMZ-DWMDIXPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  228
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  3'-deoxythymidin-3'-ylsulfamoyl-[3'(N)->5'(O)]-3'-O-acetylthymidine 以 水 为溶剂， 反应 2.0h， 生成 [(2R,4S,5R,10S,11S,13R,18R,19S)-18-hydroxy-11-(hydroxymethyl)-18,24-dimethyl-8,8,15,17,22-pentaoxo-7,12,26-trioxa-8lambda6-thia-1,9,14,16,21-pentazapentacyclo[18.2.2.12,5.110,13.014,19]hexacosa-20,23-dien-4-yl] acetate 、 [(1R,6S,7S,8R,9R,14R,16S,17S,22R,23S)-16-(hydroxymethyl)-6,9-dimethyl-3,5,10,12,19,19-hexaoxo-15,20,25-trioxa-19lambda6-thia-2,4,11,13,18-pentazahexacyclo[20.2.1.114,17.02,7.06,9.08,13]hexacosan-23-yl] acetate
  参考文献：
  名称：

  Crystal Structure and Photochemical Behavior in Solution of the 3‘-N-Sulfamate Analogue of Thymidylyl(3‘-5‘)thymidine

  摘要：

  [GRAPHICS]The 3'-N-sulfamate analogue of thymidylyl(3'-5')thymidine (TnsoT, 1) exhibits a preference for a C3'-endo conformation in the solution and solid states. Its photochemical behavior in solution is compared to that of its natural counterpart, thymidylyl(3'-5')thymidine (TpT, 2), to get further insight into the significance of the C3'-endo conformation on the photoproduct formation at the single-stranded dinucleotide level. Irradiation at 254 nm of 1 led to the same type of photoproducts as observed with 2. However, 1 was significantly more photoreactive than 2, and accordingly, the initial rate of photoproduct formation was enhanced in accordance with its propensity to base stack compared to 2. The corresponding quantum yields were determined and showed that the enhancement factor (1 compared to 2) is moderate for the cyclobutane pyrimidine dimer (CPD) (1.26) and much higher for the (6-4) photoproduct (1.8). These data strongly suggest that the CPD and (6-4) photoproduct arise from distinct minor stacked conformations.

  DOI：

  10.1021/jo061488a
• 作为产物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-3'-deoxythymidine-3'-sulfamate 在 4 A molecular sieve 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 3'-deoxythymidin-3'-ylsulfamoyl-[3'(N)->5'(O)]-3'-O-acetylthymidine
  参考文献：
  名称：

  Crystal Structure and Photochemical Behavior in Solution of the 3‘-N-Sulfamate Analogue of Thymidylyl(3‘-5‘)thymidine

  摘要：

  [GRAPHICS]The 3'-N-sulfamate analogue of thymidylyl(3'-5')thymidine (TnsoT, 1) exhibits a preference for a C3'-endo conformation in the solution and solid states. Its photochemical behavior in solution is compared to that of its natural counterpart, thymidylyl(3'-5')thymidine (TpT, 2), to get further insight into the significance of the C3'-endo conformation on the photoproduct formation at the single-stranded dinucleotide level. Irradiation at 254 nm of 1 led to the same type of photoproducts as observed with 2. However, 1 was significantly more photoreactive than 2, and accordingly, the initial rate of photoproduct formation was enhanced in accordance with its propensity to base stack compared to 2. The corresponding quantum yields were determined and showed that the enhancement factor (1 compared to 2) is moderate for the cyclobutane pyrimidine dimer (CPD) (1.26) and much higher for the (6-4) photoproduct (1.8). These data strongly suggest that the CPD and (6-4) photoproduct arise from distinct minor stacked conformations.

  DOI：

  10.1021/jo061488a