1-[3-O-(tert-butyldimethylsilyl)-2,5-dideoxy-5-C-methylene-β-D-erythro-hexofuranosylurononitrile]thymine | 405082-20-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-[3-O-(tert-butyldimethylsilyl)-2,5-dideoxy-5-C-methylene-β-D-erythro-hexofuranosylurononitrile]thymine
• 英文别名: 2-[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]prop-2-enenitrile
• CAS: 405082-20-4
• 化学式: C₁₈H₂₇N₃O₄Si
• 分子量: 377.516
• InChiKey: YUIAYGYWYKQQFV-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  91.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[3-O-(tert-butyldimethylsilyl)-2,5-dideoxy-5-C-methylene-β-D-erythro-hexofuranosylurononitrile]thymine 在 三乙胺 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 6.0h， 生成 2-[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]-3-phenylselanylpropanenitrile
  参考文献：
  名称：

  SYNTHESIS AND ANTI-HIV ACTIVITY OF THYMIDINE ANALOGUES BEARING A 4?-CYANOVINYL GROUP AND SOME DERIVATIVES THEREOF

  摘要：

  Treatment of 3'-O-tert-butyldimethylsilyl-2,5'-dideoxy-5'-oxothymidine (4) with potassium or magnesium nitromethanide afforded in good yield the resolvable epimeric mixture of the expected blocked nitronucleosides 5 which upon dehydration led to the corresponding E-nitroenofuranosylthymidine 6. Nucleophilic attack of cyanide onto the nitrovinyl group led to a nucleoside analogue bearing a terminal 1-cyanovinyl group (7), a soft electrophilic group which, upon reaction with benzeneselenol, underwent a conjugate addition to the phenylselenonucleoside derivative 9. All these compounds, eventually de-O-silylated, were subject of in vitro biological testing, some exhibiting interesting cytotoxic or antiviral properties.

  DOI：

  10.1081/ncn-100108323
• 作为产物：
  描述：

  1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(1-hydroxy-2-nitroethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 sodium acetate 、 四丁基硫酸氢铵 、 乙酸酐 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 8.0h， 生成 1-[3-O-(tert-butyldimethylsilyl)-2,5-dideoxy-5-C-methylene-β-D-erythro-hexofuranosylurononitrile]thymine
  参考文献：
  名称：

  SYNTHESIS AND ANTI-HIV ACTIVITY OF THYMIDINE ANALOGUES BEARING A 4?-CYANOVINYL GROUP AND SOME DERIVATIVES THEREOF

  摘要：

  Treatment of 3'-O-tert-butyldimethylsilyl-2,5'-dideoxy-5'-oxothymidine (4) with potassium or magnesium nitromethanide afforded in good yield the resolvable epimeric mixture of the expected blocked nitronucleosides 5 which upon dehydration led to the corresponding E-nitroenofuranosylthymidine 6. Nucleophilic attack of cyanide onto the nitrovinyl group led to a nucleoside analogue bearing a terminal 1-cyanovinyl group (7), a soft electrophilic group which, upon reaction with benzeneselenol, underwent a conjugate addition to the phenylselenonucleoside derivative 9. All these compounds, eventually de-O-silylated, were subject of in vitro biological testing, some exhibiting interesting cytotoxic or antiviral properties.

  DOI：

  10.1081/ncn-100108323