((2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl dihydrogen borate | 1227735-49-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: ((2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl dihydrogen borate
• CAS: 1227735-49-0
• 化学式: C₁₀H₁₃BN₂O₆
• 分子量: 268.034
• InChiKey: MGPXDPRHNPYEAK-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.72
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  113.78
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  司他夫定 在 dimethyl sulfide borane 、 水 作用下， 以 二氯甲烷 、 二甲基亚砜 、 四氢呋喃 为溶剂， 反应 26.0h， 以95%的产率得到((2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl)methyl dihydrogen borate
  参考文献：
  名称：

  The synthesis and NMR investigation on novel boron derivatives of stavudine

  摘要：

  Preparation and spectroscopic properties of novel boron-containing derivatives of anti-HIV agent stavudine are presented, The new compounds, (5'-O-(4,4,5,5-tetramethyl-1,3,2-dioxaboronate)-2'-3'-didehydro-2'-3'-dideoxythymidine and 5'-O-(dihydroxyboronate)-2'-3'-didehydro-2'-3'-dideoxythymidine), were prepared by direct reaction between stavudine and reagents containing B-H moieties - pinacolborane and borane-dimethylsulfide complexes, respectively. The boron coordination equilibrium of those compounds was analyzed by water titration monitored by NMR. Results of the DFT calculations and NMR experiments pointed to structural and electronic similarity of tetrahedral boron complexes to phosphate group. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2009.12.005