9-(3-duterio-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)adenine | 90124-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-(3-duterio-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)adenine
• 英文别名: 9-(2,3-Dideoxy-3-deuterio-β-D-glycero-pent-2-enofuranosyl)adenine；[(2S,5R)-5-(6-aminopurin-9-yl)-3-deuterio-2,5-dihydrofuran-2-yl]methanol
• CAS: 90124-47-3
• 化学式: C₁₀H₁₁N₅O₂
• 分子量: 234.222
• InChiKey: JFUOUIPRAAGUGF-XIVNSHSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  99.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-(3-duterio-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)adenine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 19.0~22.0 ℃ 、68.94 kPa 条件下， 反应 5.0h， 以80%的产率得到9-(2,3-Dideoxy-3-deuterio-β-D-glycero-pentofuranosyl)adenine
  参考文献：
  名称：

  Nucleic Acid-Related Compounds. 88. Efficient Conversions of Ribonucleosides into Their 2',3'-Anhydro, 2'(and 3')-Deoxy, 2',3'-Didehydro-2',3'-dideoxy, and 2',3'-Dideoxynucleoside Analogs

  摘要：

  Treatment of purine, pyrimidine, and modified purine (antibiotic) ribonucleosides with 2-acetoxy-2-methylpropanoyl (alpha-acetoxyisobutyryl) bromide in acetonitrile gave mixtures of 2',3'-bromohydrin acetates with different O5' substituents. Significant amounts of 5'-unprotected (hydroxyl) bromo acetates were obtained in some cases, and formation of 2',3'-O-isopropylidene derivatives as minor byproducts was detected for the first time. Acid-catalyzed nucleophilic displacement of chloride by bromide occurred with 2-amino-6-chloropurine riboside, but no substitution of fluoride by bromide was detected with 6-amino-2-fluoropurine riboside. Treatment of the trans bromo acetate mixtures obtained from purine-type nucleosides with Dowex 1 x 2 (OH-) in methanol gave the 2',3'-anhydro (ribo epoxide) compounds. Radical-mediated hydrogenolytic debromination and deprotection gave 2'- and 3'-deoxynucleosides. Treatment of the bromo acetate mixtures with zinc-copper couple or acetic acid-activated zinc effected reductive elimination, and deprotection gave 2',3'-didehydro-2',3'-dideoxy compounds which were hydrogenated to give 2',3'-dideoxynucleosides. A number of these analogues have potent inhibitory activity against AIDS and hepatitis B viruses. New C-13 NMR data for several types of unsaturated-sugar nucleosides are tabulated. These procedures are directly applicable for the preparation of L-didehydro-dideoxy and L-dideoxy nucleoside analogues.

  DOI：

  10.1021/jo00129a034
• 作为产物：
  描述：

  3'-deuterioadenosine 生成 9-(3-duterio-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)adenine
  参考文献：
  名称：

  A mild conversion of vicinal diols to alkenes. Efficient transformation of ribonucleosides into 2′-ene and 2t',3′-dideoxynucleosides

  摘要：

  DOI：

  10.1016/s0040-4039(00)99885-x

文献信息

• A mild conversion of vicinal diols to alkenes. Efficient transformation of ribonucleosides into 2′-ene and 2t',3′-dideoxynucleosides
  作者：Morris J. Robins、Fritz Hansske、Nicholas H. Low、Ja In Park

  DOI：10.1016/s0040-4039(00)99885-x

  日期：1984.1
• Nucleic Acid-Related Compounds. 88. Efficient Conversions of Ribonucleosides into Their 2',3'-Anhydro, 2'(and 3')-Deoxy, 2',3'-Didehydro-2',3'-dideoxy, and 2',3'-Dideoxynucleoside Analogs
  作者：Morris J. Robins、John S. Wilson、Danuta Madej、Nicholas H. Low、Fritz Hansske、Stanislaw F. Wnuk

  DOI：10.1021/jo00129a034

  日期：1995.12

  Treatment of purine, pyrimidine, and modified purine (antibiotic) ribonucleosides with 2-acetoxy-2-methylpropanoyl (alpha-acetoxyisobutyryl) bromide in acetonitrile gave mixtures of 2',3'-bromohydrin acetates with different O5' substituents. Significant amounts of 5'-unprotected (hydroxyl) bromo acetates were obtained in some cases, and formation of 2',3'-O-isopropylidene derivatives as minor byproducts was detected for the first time. Acid-catalyzed nucleophilic displacement of chloride by bromide occurred with 2-amino-6-chloropurine riboside, but no substitution of fluoride by bromide was detected with 6-amino-2-fluoropurine riboside. Treatment of the trans bromo acetate mixtures obtained from purine-type nucleosides with Dowex 1 x 2 (OH-) in methanol gave the 2',3'-anhydro (ribo epoxide) compounds. Radical-mediated hydrogenolytic debromination and deprotection gave 2'- and 3'-deoxynucleosides. Treatment of the bromo acetate mixtures with zinc-copper couple or acetic acid-activated zinc effected reductive elimination, and deprotection gave 2',3'-didehydro-2',3'-dideoxy compounds which were hydrogenated to give 2',3'-dideoxynucleosides. A number of these analogues have potent inhibitory activity against AIDS and hepatitis B viruses. New C-13 NMR data for several types of unsaturated-sugar nucleosides are tabulated. These procedures are directly applicable for the preparation of L-didehydro-dideoxy and L-dideoxy nucleoside analogues.