2',3'-Di-O-acetyl-5'-fluoro-5'-S-(4-methoxyphenyl)-5'-thioadenosine | 121517-97-3

• 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'-fluoro-5'-S-(4-methoxyphenyl)-5'-thioadenosine
• 英文别名: [(2S,3S,4R,5R)-4-acetyloxy-5-(6-aminopurin-9-yl)-2-[fluoro-(4-methoxyphenyl)sulfanylmethyl]oxolan-3-yl] acetate
• CAS: 121517-97-3；121524-25-2
• 化学式: C₂₁H₂₂FN₅O₆S
• 分子量: 491.5
• InChiKey: BFTPIKJPXYQTKH-KLUZDXMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  166
• 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'-fluoro-5'-S-(4-methoxyphenyl)-5'-thioadenosine 在 吡啶 、 氨 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 11.75h， 生成 2',3'-Di-O-acetyl-5'(S)-fluoro-5'-<(4-methoxyphenyl)sulfinyl>(S_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：

  2',3'-Di-O-acetyl-5'-S-(4-methoxyphenyl)-5'-thioadenosine 在 三氯化锑 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 2',3'-Di-O-acetyl-5'-fluoro-5'-S-(4-methoxyphenyl)-5'-thioadenosine
  参考文献：
  名称：

  Nucleic acid related compounds. 79. Efficient conversions of thioethers to .alpha.-fluoro thioethers with DAST or DAST/antimony(III) chloride

  摘要：

  Dialkyl or alkyl aryl thioethers, including nucleoside thioethers, undergo virtually quantitative conversion to alpha-fluoro thioethers with (diethylamino)sulfur trifluoride (DAST) in dichloromethane at ambient temperature. Antimony(III) chloride catalyzes the process.

  DOI：

  10.1021/jo00067a009

文献信息

• Fluorination at C5′ of nucleosides. Synthesis of the new class of 5′-fluoro-5′-S-aryl (alkyl) thionucleosides from adenosine.
  作者：Morris J. Robins、Wnuk F. Stanislaw

  DOI：10.1016/s0040-4039(00)82174-7

  日期：1988.1
• 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：——