5-chloro-4-methoxy-1-(5-O-tert-butyldimethylsilyl-2-deoxy-β-D-erythro-pentofuranosyl)pyridazin-6-one | 156549-54-1

• 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: 5-chloro-4-methoxy-1-(5-O-tert-butyldimethylsilyl-2-deoxy-β-D-erythro-pentofuranosyl)pyridazin-6-one
• CAS: 156549-54-1
• 化学式: C₁₆H₂₇ClN₂O₅Si
• 分子量: 390.939
• InChiKey: PNMVQGHYVLHTNF-CYZMBNFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  82.81
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-chloro-4-methoxy-1-(5-O-tert-butyldimethylsilyl-2-deoxy-β-D-erythro-pentofuranosyl)pyridazin-6-one 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 51.0h， 生成 5-chloro-4-methoxy-1-(5-O-tert-butyldimethylsilyl-2,3-dideoxy-β-D-glycero-pentofuranosyl)pyridazin-6-one
  参考文献：
  名称：

  Synthesis of 2′,3′-Dideoxy- and 3′-Azido-2′,3′-dideoxy-pyridazine Nucleosides as Potential Antiviral Agents

  摘要：

  The synthesis of 4-methoxy-, 4-amino-3-chloro-, and 4-amino-1-(2,3-dideoxy-beta-D-glycero-pentofuranosyl)pyridazin-6-one nucleosides, 6, 19 and 20 is described. The synthesis of 3,4-dichloropyridazin-6-one (10) was accomplished in 44% overall yield using bromomaleic anhydride (17) as the starting material. The condensation of the silylated base of 10 with the halogenose 12 in the presence of trimethylsilyl triflate as a catalyst afforded a mixture of 3,4-dichloro-1-(3,5-di-O-p-toluoyl-2-deoxy-beta-D-erythro-pentofuranosyl)pyridazin-6-one (13) in 67% and its alpha-anomer 14 in 12% yield, (r)espectively. A series of 3'-sulfonate esters were prepared to explore the synthesis of 3-chloro-4-hydroxy-1- (3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)pyridazin-6-one (32) via 6,3-anhydronucleoside analogues. Compounds 15, 19 and 20 were evaluated against human immunodeficiency virus, human cytomegalovirus, and herpes simplex virus type 1 but were inactive.

  DOI：

  10.1080/15257779408013255
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 4-chloro-2-(2'-deoxy-β-D-erythro-pentofuranosyl)-5-methoxypyridazin-3(2H)-one 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以86%的产率得到5-chloro-4-methoxy-1-(5-O-tert-butyldimethylsilyl-2-deoxy-β-D-erythro-pentofuranosyl)pyridazin-6-one
  参考文献：
  名称：

  Synthesis of 2′,3′-Dideoxy- and 3′-Azido-2′,3′-dideoxy-pyridazine Nucleosides as Potential Antiviral Agents

  摘要：

  The synthesis of 4-methoxy-, 4-amino-3-chloro-, and 4-amino-1-(2,3-dideoxy-beta-D-glycero-pentofuranosyl)pyridazin-6-one nucleosides, 6, 19 and 20 is described. The synthesis of 3,4-dichloropyridazin-6-one (10) was accomplished in 44% overall yield using bromomaleic anhydride (17) as the starting material. The condensation of the silylated base of 10 with the halogenose 12 in the presence of trimethylsilyl triflate as a catalyst afforded a mixture of 3,4-dichloro-1-(3,5-di-O-p-toluoyl-2-deoxy-beta-D-erythro-pentofuranosyl)pyridazin-6-one (13) in 67% and its alpha-anomer 14 in 12% yield, (r)espectively. A series of 3'-sulfonate esters were prepared to explore the synthesis of 3-chloro-4-hydroxy-1- (3-azido-2,3-dideoxy-beta-D-erythro-pentofuranosyl)pyridazin-6-one (32) via 6,3-anhydronucleoside analogues. Compounds 15, 19 and 20 were evaluated against human immunodeficiency virus, human cytomegalovirus, and herpes simplex virus type 1 but were inactive.

  DOI：

  10.1080/15257779408013255