7-chloro-3-<2,3-dideoxy-5-O-<(dimethylethyl)diphenylsilyl>-β-D-glycero-pentofuranosyl>-3H-1,2,3-triazolo<4,5-b>pyridine | 162299-73-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 7-chloro-3-<2,3-dideoxy-5-O-<(dimethylethyl)diphenylsilyl>-β-D-glycero-pentofuranosyl>-3H-1,2,3-triazolo<4,5-b>pyridine
• CAS: 162299-73-2
• 化学式: C₂₆H₂₉ClN₄O₂Si
• 分子量: 493.08
• InChiKey: CVNCWFXOZQGWIE-WMZHIEFXSA-N

物化性质

• 沸点：
  582.8±50.0 °C(predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  7-chloro-3-<2,3-dideoxy-5-O-<(dimethylethyl)diphenylsilyl>-β-D-glycero-pentofuranosyl>-3H-1,2,3-triazolo<4,5-b>pyridine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以61%的产率得到7-chloro-3-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-3H-1,2,3-triazolo<4,5-b>pyridine
  参考文献：
  名称：

  8-Aza-1-deazapurine Nucleosides as Antiviral Agents

  摘要：

  2',3'-Dideoxy-8-aza-1-deazaadenosine (21) and its alpha-anomer (20) were synthesized via glycosylation of 7-chloro-3H-1,2,3-triazolo[4,5-b]pyridine with 2,3-dideoxy-5-0-[(1,1)-dimethylethyl)diphenylsilyl]-D-glycero-pentofuranosyl chloride. The reaction gave a mixture of alpha- and beta-anomers of N-3-, N-2- and N-1-glycosylated regioisomers (12-15). The alpha- and beta-anomers of the N-4-glycosylated isomer 26 and 27 were also synthesized through the glycosylation of 8-aza-1-deazaadenine with 1-acetoxy-2,3-dideoxy-5-0-[(1,1-dimethylethyl)dimethylsilyl]-D-glycero-pen. These dideoxynucleosides and a series of previously synthesized 8-aza-1-deazapurine nucleosides were tested for activity against several DNA and RNA viruses, HIV-1 included. The alpha- and beta-anomers of 7-chloro-3-(2-deoxy-D-erythro-pentofuranosyl)-3H-1,2,3-triazolo[4,5-b]pyridine (3a and 4) showed activities against Sb-1 and Coxs viruses. The alpha- and beta-anomers of 2',3'-dideoxy-8-aza-1-deazaadenosine (20 and 21) were found active as inhibitors of adenosine deaminase.

  DOI：

  10.1080/15257779408009477
• 作为产物：
  描述：

  7-氯-3-三唑并(1,2,3)[4,5-b]吡啶 、 2,3-dideoxy-5-O-<(1,1-dimethylethyl)diphenylsilyl>-α-D-glycero-pentofuranosyl chloride 在 氢氧化钾 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 5.0h， 以12%的产率得到7-chloro-3-<2,3-dideoxy-5-O-<(dimethylethyl)diphenylsilyl>-β-D-glycero-pentofuranosyl>-3H-1,2,3-triazolo<4,5-b>pyridine
  参考文献：
  名称：

  8-Aza-1-deazapurine Nucleosides as Antiviral Agents

  摘要：

  2',3'-Dideoxy-8-aza-1-deazaadenosine (21) and its alpha-anomer (20) were synthesized via glycosylation of 7-chloro-3H-1,2,3-triazolo[4,5-b]pyridine with 2,3-dideoxy-5-0-[(1,1)-dimethylethyl)diphenylsilyl]-D-glycero-pentofuranosyl chloride. The reaction gave a mixture of alpha- and beta-anomers of N-3-, N-2- and N-1-glycosylated regioisomers (12-15). The alpha- and beta-anomers of the N-4-glycosylated isomer 26 and 27 were also synthesized through the glycosylation of 8-aza-1-deazaadenine with 1-acetoxy-2,3-dideoxy-5-0-[(1,1-dimethylethyl)dimethylsilyl]-D-glycero-pen. These dideoxynucleosides and a series of previously synthesized 8-aza-1-deazapurine nucleosides were tested for activity against several DNA and RNA viruses, HIV-1 included. The alpha- and beta-anomers of 7-chloro-3-(2-deoxy-D-erythro-pentofuranosyl)-3H-1,2,3-triazolo[4,5-b]pyridine (3a and 4) showed activities against Sb-1 and Coxs viruses. The alpha- and beta-anomers of 2',3'-dideoxy-8-aza-1-deazaadenosine (20 and 21) were found active as inhibitors of adenosine deaminase.

  DOI：

  10.1080/15257779408009477