1-[5-O-(tert-butyldimethylsilyl)-2-deoxy-3-O-[(methylthio)thiocarbonyl]-β-D-erythro-pentofuranosyl]thymine | 928761-36-8

• 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: 1-[5-O-(tert-butyldimethylsilyl)-2-deoxy-3-O-[(methylthio)thiocarbonyl]-β-D-erythro-pentofuranosyl]thymine
• 英文别名: O-[(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] methylsulfanylmethanethioate
• CAS: 928761-36-8
• 化学式: C₁₈H₃₀N₂O₅S₂Si
• 分子量: 446.664
• InChiKey: ZZIFKQQPRBIFKZ-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[5-O-(tert-butyldimethylsilyl)-2-deoxy-3-O-[(methylthio)thiocarbonyl]-β-D-erythro-pentofuranosyl]thymine 、 丙烯腈 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 9.5h， 以25%的产率得到1-[5-O-(tert-butyldimethylsilyl)-3-C-(2-cyanoethyl)-2,3-dideoxy-β-D-erythro-pentofuranosyl]thymine
  参考文献：
  名称：

  Synthesis of 3′-C-substituted thymidine derivatives by free-radical techniques: scope and limitations

  摘要：

  The scope and limitations of radical-mediated 3'-C-substitution of pyrimidine nucleosides was evaluated with 5'-O-(tertbutyldimethylsilyl)thymidine or its tert-butyldiphenylsilyl analogue having thionoester or thionoamide groups at O-3', including (methylthio)thiocarbonyl, (phenoxy)thiocarbonyl, (pentafluorophenoxy)thiocarbonyl, and (1-imidazoiyl)thiocarbonyl. Their reaction with acrylonitrile, methyl acrylate, and allyltributyltin under radical-generating conditions affords corresponding 3'-C-alkylated products, together with the product of simple deoxygenation at C-3'. The conditions for optimizing the yield of 3'-C-substituted product are presented. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.11.015
• 作为产物：
  描述：

  beta-胸苷 在 咪唑 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1-[5-O-(tert-butyldimethylsilyl)-2-deoxy-3-O-[(methylthio)thiocarbonyl]-β-D-erythro-pentofuranosyl]thymine
  参考文献：
  名称：

  Synthesis of 3′-C-substituted thymidine derivatives by free-radical techniques: scope and limitations

  摘要：

  The scope and limitations of radical-mediated 3'-C-substitution of pyrimidine nucleosides was evaluated with 5'-O-(tertbutyldimethylsilyl)thymidine or its tert-butyldiphenylsilyl analogue having thionoester or thionoamide groups at O-3', including (methylthio)thiocarbonyl, (phenoxy)thiocarbonyl, (pentafluorophenoxy)thiocarbonyl, and (1-imidazoiyl)thiocarbonyl. Their reaction with acrylonitrile, methyl acrylate, and allyltributyltin under radical-generating conditions affords corresponding 3'-C-alkylated products, together with the product of simple deoxygenation at C-3'. The conditions for optimizing the yield of 3'-C-substituted product are presented. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.11.015