Acetic acid (2S,3S,4R,5R)-4,5-diacetoxy-2-(1,3-dimethyl-2-oxo-6-thioxo-1,2,3,6-tetrahydro-purin-7-yl)-tetrahydro-pyran-3-yl ester | 181206-33-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2S,3S,4R,5R)-4,5-diacetoxy-2-(1,3-dimethyl-2-oxo-6-thioxo-1,2,3,6-tetrahydro-purin-7-yl)-tetrahydro-pyran-3-yl ester
• 英文别名: [(3R,4R,5S,6S)-4,5-diacetyloxy-6-(1,3-dimethyl-2-oxo-6-sulfanylidenepurin-7-yl)oxan-3-yl] acetate
• CAS: 181206-33-7
• 化学式: C₁₈H₂₂N₄O₈S
• 分子量: 454.461
• InChiKey: BSPRFBLTIWSSLK-UYHMYPTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  162
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3S,4R,5R)-4,5-diacetoxy-2-(1,3-dimethyl-2-oxo-6-thioxo-1,2,3,6-tetrahydro-purin-7-yl)-tetrahydro-pyran-3-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以70%的产率得到1,3-Dimethyl-6-thioxo-7-((2S,3S,4R,5R)-3,4,5-trihydroxy-tetrahydro-pyran-2-yl)-1,3,6,7-tetrahydro-purin-2-one
  参考文献：
  名称：

  Synthesis of 7-(β-D-Glucopyranosyl)-6-Thiotheophylline and 7-(α-D-Arabinopyranosyl)-6-Thiotheopwlline. Conformational Study of the Peracetyl Derivatives.

  摘要：

  The synthesis of two 7-glycosyl-6-thiotheophylline nucleosides where the sugar moieties are beta-D-glucose (1b) and alpha-D-arabinose (2b) is reported. The syn-anti equilibrium of the peracetyl derivatives was studied by the line-shape and the H-1-NMR nOe methods, and molecular mechanics analysis.

  DOI：

  10.1080/07328319608002440
• 作为产物：
  描述：

  7-α-D-arabinopyranosyltheophylline 在 劳森试剂 作用下， 以 吡啶 、 甲苯 为溶剂， 反应 24.0h， 生成 Acetic acid (2S,3S,4R,5R)-4,5-diacetoxy-2-(1,3-dimethyl-2-oxo-6-thioxo-1,2,3,6-tetrahydro-purin-7-yl)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of 7-(β-D-Glucopyranosyl)-6-Thiotheophylline and 7-(α-D-Arabinopyranosyl)-6-Thiotheopwlline. Conformational Study of the Peracetyl Derivatives.

  摘要：

  The synthesis of two 7-glycosyl-6-thiotheophylline nucleosides where the sugar moieties are beta-D-glucose (1b) and alpha-D-arabinose (2b) is reported. The syn-anti equilibrium of the peracetyl derivatives was studied by the line-shape and the H-1-NMR nOe methods, and molecular mechanics analysis.

  DOI：

  10.1080/07328319608002440