Acetic acid (2S,3S,4R,5S)-4-acetoxy-5-acetoxymethyl-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-thiophen-3-yl ester | 592524-06-6

• 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: Acetic acid (2S,3S,4R,5S)-4-acetoxy-5-acetoxymethyl-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-thiophen-3-yl ester
• 英文别名: [(2S,3R,4S,5S)-3,4-diacetyloxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)thiolan-2-yl]methyl acetate
• CAS: 592524-06-6
• 化学式: C₁₆H₂₀N₂O₈S
• 分子量: 400.409
• InChiKey: LFJHZQRAOHBXSN-ABHRYQDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  154
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3S,4R,5S)-4-acetoxy-5-acetoxymethyl-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-thiophen-3-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以90%的产率得到1-((2S,3S,4R,5S)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-thiophen-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of some novel 4′-Thio-l-ribonucleosides with modified nucleobase moieties

  摘要：

  1,2,3,5-Tetra-O-acetyl-4-thio-beta-L-ribofuranose (13) was synthesized by an improved five-step sequence starting from methyl alpha-D-lyxopyranoside. Compound 13 was then converted to the corresponding L-4'-thionucleosides 4-6 and 19 by a modified Vorbruggen procedure. All of these nucleoside analogues were tested for their antitumour activity in vitro. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00289-0
• 作为产物：
  描述：

  胸腺嘧啶 在 硫酸氢铵 、 三甲基氯硅烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 11.0h， 生成 Acetic acid (2S,3S,4R,5S)-4-acetoxy-5-acetoxymethyl-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-thiophen-3-yl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of some novel 4′-Thio-l-ribonucleosides with modified nucleobase moieties

  摘要：

  1,2,3,5-Tetra-O-acetyl-4-thio-beta-L-ribofuranose (13) was synthesized by an improved five-step sequence starting from methyl alpha-D-lyxopyranoside. Compound 13 was then converted to the corresponding L-4'-thionucleosides 4-6 and 19 by a modified Vorbruggen procedure. All of these nucleoside analogues were tested for their antitumour activity in vitro. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00289-0