2',3'-di-O-acetyl-5'-deoxy-5',5'-dichloroadenosine | 144494-08-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 2',3'-di-O-acetyl-5'-deoxy-5',5'-dichloroadenosine
• 英文别名: [(2S,3S,4R,5R)-4-acetyloxy-5-(6-aminopurin-9-yl)-2-(dichloromethyl)oxolan-3-yl] acetate
• CAS: 144494-08-6
• 化学式: C₁₄H₁₅Cl₂N₅O₅
• 分子量: 404.21
• InChiKey: QXDOKFKXPOUVDW-QOBXEIRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2',3'-Di-O-acetyl-5'-S-(4-methoxyphenyl)-5'-thioadenosine 在 2,3-二氯碘苯 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 生成 9-(2,3-di-O-acetyl-5-deoxy-5,5-dichloro-β-D-erythro-pent-4-enofuranosyl)adenine 、 2',3'-di-O-acetyl-5'-deoxy-5',5'-dichloroadenosine
  参考文献：
  名称：

  Nucleic acid related compounds. 76. Synthesis of 5'(E and Z)-chloro-4',5'-didehydro-5'-deoxyadenosines via chlorination and thermolysis of adenosine 5'-sulfoxides. Mechanism-based inhibition of S-adenosyl-L-homocysteine hydrolase

  摘要：

  Treatment of 2',3'-di-O-acetyl-5'-S-(4-methoxyphenyl)-5'-thioadenosine (1a), or its sulfoxides 2a(S(R)) and 3a(S(S)), with iodobenzene dichloride and potassium carbonate in acetonitrile resulted in formation of the 5'-chloro(and 5',5'-dichloro)-5'-deoxy-5'-[(4-methoxyphenyl)sulfinyl]adenosines 4a, 5a, 6a, and minor diastereomers. Deprotection of 5a gave 5'(S)-chloro-5'-deoxy-5'-[(4-methoxyphenyl)-sulfinyl(S(S))]adenosine [5b(5'S,S(S))] whose stereochemistry and conformation were established by X-ray crystallography. The alpha-chlorination of sulfoxides 2a(S(R)) and 3a (S(S)) occurred with predominant retention of configuration at sulfur. Thermolysis of the alpha-chloro sulfoxides and deprotection gave the chloromethylene derivatives. The 5'(Z)-chloro-4',5'-didehydro-5'-deoxyadenosine [9b(5'Z)] diastereomer was found to be a potent time-dependent inhibitor of S-adenosyl-L-homocysteine hydrolase.

  DOI：

  10.1021/jo00053a022

文献信息

• Nucleic acid related compounds. 76. Synthesis of 5'(E and Z)-chloro-4',5'-didehydro-5'-deoxyadenosines via chlorination and thermolysis of adenosine 5'-sulfoxides. Mechanism-based inhibition of S-adenosyl-L-homocysteine hydrolase
  作者：Stanislaw F. Wnuk、N. Kent Dalley、Morris J. Robins

  DOI：10.1021/jo00053a022

  日期：1993.1

  Treatment of 2',3'-di-O-acetyl-5'-S-(4-methoxyphenyl)-5'-thioadenosine (1a), or its sulfoxides 2a(S(R)) and 3a(S(S)), with iodobenzene dichloride and potassium carbonate in acetonitrile resulted in formation of the 5'-chloro(and 5',5'-dichloro)-5'-deoxy-5'-[(4-methoxyphenyl)sulfinyl]adenosines 4a, 5a, 6a, and minor diastereomers. Deprotection of 5a gave 5'(S)-chloro-5'-deoxy-5'-[(4-methoxyphenyl)-sulfinyl(S(S))]adenosine [5b(5'S,S(S))] whose stereochemistry and conformation were established by X-ray crystallography. The alpha-chlorination of sulfoxides 2a(S(R)) and 3a (S(S)) occurred with predominant retention of configuration at sulfur. Thermolysis of the alpha-chloro sulfoxides and deprotection gave the chloromethylene derivatives. The 5'(Z)-chloro-4',5'-didehydro-5'-deoxyadenosine [9b(5'Z)] diastereomer was found to be a potent time-dependent inhibitor of S-adenosyl-L-homocysteine hydrolase.