S_P-deoxyxylothymidyl-3'-O-acetylthymidyl (3',5')-O-(2-cyanoethyl)phosphorothioate

• 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: S_P-deoxyxylothymidyl-3'-O-acetylthymidyl (3',5')-O-(2-cyanoethyl)phosphorothioate
• 英文别名: [(2R,3S,5R)-2-[[2-cyanoethoxy-[(2R,3R,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphinothioyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
• 化学式: C₂₅H₃₂N₅O₁₂PS
• 分子量: 657.595
• InChiKey: MRAAZRBDQMVGJL-IVPHBADLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  247
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  3'-O-acetylthymidine 在 四氮唑 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 溶剂黄146 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 74.0h， 生成 S_P-deoxyxylothymidyl-3'-O-acetylthymidyl (3',5')-O-(2-cyanoethyl)phosphorothioate
  参考文献：
  名称：

  Synthesis and Structural Studies ofSP andRP Diastereomers of Deoxyxylothymidyl-3′-O-acetylthymidyl (3′,5′)-O-(2-Cyanoethyl)phosphorothioate in Solution and in the Solid State

  摘要：

  The synthesis and full assignment of the molecular structure of the diastereomers of deoxyxylothymidyl-3'-O-acetylthymidyl (3',5')-O-(2-cyanoethyl)phosphorothioate (1) in the liquid phase based on H-1, C-13, 1D and 2D homo- and heteronuclear PFG (Pulse Field Gradient) NMR spectroscopic experiments are reported. The pseudorotation parameters of deoxyribose and deoxyxylose were analyzed by means of the PSEUROT program. The absolute configuration Rp and Sp Of the phosphorus centers was deduced from H-1 ROESY experiment. The P-31 CP/MAS technique was used to establish the ratio between the amorphous and crystalline phases, and to test the progress of crystallization. The differences in the P-31 delta (ii) principal elements of the chemical shift tenser, in particular the delta (33) parameter, for crystalline and amorphous phases were calculated Finally, the X-ray data for the Sp diastereomer are reported. The influence of weak C-H S hydrogen bonding on the molecular packing of both R-p-1 and S-P-1, and the significance of this type of intermolecular interaction for phosphorothioate systems is discussed.

  DOI：

  10.1002/1099-0690(200104)2001:8<1491::aid-ejoc1491>3.0.co;2-3

文献信息

• Synthesis and Structural Studies ofSP andRP Diastereomers of Deoxyxylothymidyl-3′-O-acetylthymidyl (3′,5′)-O-(2-Cyanoethyl)phosphorothioate in Solution and in the Solid State
  作者：Marek J. Potrzebowski、Xian-Bin Yang、Konrad Misiura、Wieslaw R. Majzner、Michal W. Wieczorek、Slawomir Kaźmierski、Sebastian Olejniczak、Wojciech J. Stec

  DOI：10.1002/1099-0690(200104)2001:8<1491::aid-ejoc1491>3.0.co;2-3

  日期：2001.4

  The synthesis and full assignment of the molecular structure of the diastereomers of deoxyxylothymidyl-3'-O-acetylthymidyl (3',5')-O-(2-cyanoethyl)phosphorothioate (1) in the liquid phase based on H-1, C-13, 1D and 2D homo- and heteronuclear PFG (Pulse Field Gradient) NMR spectroscopic experiments are reported. The pseudorotation parameters of deoxyribose and deoxyxylose were analyzed by means of the PSEUROT program. The absolute configuration Rp and Sp Of the phosphorus centers was deduced from H-1 ROESY experiment. The P-31 CP/MAS technique was used to establish the ratio between the amorphous and crystalline phases, and to test the progress of crystallization. The differences in the P-31 delta (ii) principal elements of the chemical shift tenser, in particular the delta (33) parameter, for crystalline and amorphous phases were calculated Finally, the X-ray data for the Sp diastereomer are reported. The influence of weak C-H S hydrogen bonding on the molecular packing of both R-p-1 and S-P-1, and the significance of this type of intermolecular interaction for phosphorothioate systems is discussed.