2',3'-Di-O-acetyl-5'-deoxy-5'-<(4-methoxyphenyl)sulfinyl>adenosine | 121517-95-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2',3'-Di-O-acetyl-5'-deoxy-5'-<(4-methoxyphenyl)sulfinyl>adenosine
• 英文别名: [(2S,3S,4R,5R)-4-acetyloxy-5-(6-aminopurin-9-yl)-2-[(4-methoxyphenyl)sulfinylmethyl]oxolan-3-yl] acetate
• CAS: 121517-95-1；121517-96-2
• 化学式: C₂₁H₂₃N₅O₇S
• 分子量: 489.509
• InChiKey: FKPXJBACIJQFLK-LGXGWTMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  177
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2',3'-Di-O-acetyl-5'-deoxy-5'-<(4-methoxyphenyl)sulfinyl>adenosine 在 三氯化锑 (diethylamido)sulfur trifluoride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 10.75h， 生成 2',3'-Di-O-acetyl-5'(S)-fluoro-5'-<(4-methoxyphenyl)sulfinyl>(R_S)adenosine
  参考文献：
  名称：

  Nucleic Acid Related Compounds. 80. Synthesis of 5'-S-(Alkyl and aryl)-5'-fluoro-5'-thioadenosines with Xenon Difluoride or (Diethylamido)sulfur Trifluoride, Hydrolysis in Aqueous Buffer, and Inhibition of S-Adenosyl-L-homocysteine hydrolase by derived "Adenosine 5'-Aldehyde" Species

  摘要：

  Treatment of 5/-S-(alkyl and aryl)-5'-thioadenosine derivatives 2 with XeF2, or the corresponding sulfoxides 3 with DAST/SbCl3, gave diastereomeric 5'-fluoro compounds which were deprotected to give the 5'-S-(alkyl and aryl)-5'-fluoro-5'-thioadenosine analogues 5. Stereochemistry was established by X-ray crystallography, and F-19 NMR chemical shifts were definitive for configurationally-related 5'-fluoro diastereomers. Sulfoxidation and thermolysis afforded the fluoromethylene analogues with retained relative configuration. The nucleoside 5'-alpha-fluoro thioethers 5 underwent spontaneous hydrolysis in aqueous buffer to give derived ''adenosine 5'-aldehyde'' species which caused potent time-dependent inactivation of S-adenosyl-L-homocysteine hydrolase.

  DOI：

  10.1021/jo00082a010
• 作为产物：
  描述：

  5'-氯-5'-脱氧腺苷 在 吡啶 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2',3'-Di-O-acetyl-5'-deoxy-5'-<(4-methoxyphenyl)sulfinyl>adenosine
  参考文献：
  名称：

  Fluorination at C5′ of nucleosides. Synthesis of the new class of 5′-fluoro-5′-S-aryl (alkyl) thionucleosides from adenosine.

  摘要：

  DOI：

  10.1016/s0040-4039(00)82174-7

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.
• ROBINS, MORRIS J.;WNUK, STANISLAW F., TETRAHEDRON LETT., 29,(1988) N 45, C. 5729-5732
  作者：ROBINS, MORRIS J.、WNUK, STANISLAW F.

  DOI：——

  日期：——