1-[(E)-3-O-(tert-butyldimethylsilyl)-2,5,6-trideoxy-6-nitro-β-D-erythro-hex-5-enofuranosyl]thymine | 405082-19-1

• 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-[(E)-3-O-(tert-butyldimethylsilyl)-2,5,6-trideoxy-6-nitro-β-D-erythro-hex-5-enofuranosyl]thymine
• 英文别名: 1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[(E)-2-nitroethenyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 405082-19-1
• 化学式: C₁₇H₂₇N₃O₆Si
• 分子量: 397.503
• InChiKey: VAFSZEDOOWMHNP-CFACAHNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(E)-3-O-(tert-butyldimethylsilyl)-2,5,6-trideoxy-6-nitro-β-D-erythro-hex-5-enofuranosyl]thymine 在 sodium acetate 、 四丁基硫酸氢铵 、 三乙胺 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 1.0h， 生成 2-[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-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 、 乙酸酐 作用下， 反应 8.0h， 以76%的产率得到1-[(E)-3-O-(tert-butyldimethylsilyl)-2,5,6-trideoxy-6-nitro-β-D-erythro-hex-5-enofuranosyl]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

文献信息

• SYNTHESIS AND ANTI-HIV ACTIVITY OF THYMIDINE ANALOGUES BEARING A 4?-CYANOVINYL GROUP AND SOME DERIVATIVES THEREOF
  作者：Jean Tronchet、Imre Kovacs、Pierre Dilda、Michel Seman、Graciela Andrei、Robert Snoeck、Erik De Clercq、Jan Balzarini

  DOI：10.1081/ncn-100108323

  日期：——

  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.