9-<2',3'-Di-O-acetyl-5'(E)-O-Methyl-β-D-erythro-pent-4-enofuranosyl>adenine | 153920-19-5

• 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-<2',3'-Di-O-acetyl-5'(E)-O-Methyl-β-D-erythro-pent-4-enofuranosyl>adenine
• 英文别名: [(2R,3R,4S,5E)-4-acetyloxy-2-(6-aminopurin-9-yl)-5-(methoxymethylidene)oxolan-3-yl] acetate
• CAS: 153920-19-5
• 化学式: C₁₅H₁₇N₅O₆
• 分子量: 363.33
• InChiKey: PNDSKSRTXXRAHY-IMCDHCNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  9-<2',3'-Di-O-acetyl-5'(E)-O-Methyl-β-D-erythro-pent-4-enofuranosyl>adenine 在 氨 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 9-<5(E)-O-Methyl-β-D-erythro-pent-4-enofuranosyl>adenine
  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'-deoxy-5'-(methylthio)adenosine 在 三氯化锑 吡啶 、 (diethylamido)sulfur trifluoride 、 氨 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 二乙二醇二甲醚 为溶剂， 反应 23.0h， 生成 9-<2',3'-Di-O-acetyl-5'(E)-O-Methyl-β-D-erythro-pent-4-enofuranosyl>adenine
  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