-S-methyl adenosine 3',5'-cyclophosphorothioate | 172907-81-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: -S-methyl adenosine 3',5'-cyclophosphorothioate
• CAS: 172907-81-2
• 化学式: C₁₁H₁₄N₅O₅PS
• 分子量: 359.302
• InChiKey: UERURTBLNCMDML-IOIQHYAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.55
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  134.61
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  -S-methyl adenosine 3',5'-cyclophosphorothioate 在 吡啶 、 silver fluoride 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 3.0h， 生成 -adenosine cyclic 3',5'-phosphorofluoridate
  参考文献：
  名称：

  Synthesis of adenosine cyclic 3ȃ,5ȃ-phosphorof)uoridate (camp-f)

  摘要：

  Work aimed at the chiral synthesis of both diastereomers of adenosine cyclic 3',5'-phosphorofluoridate, cAMP-F 7, is described. Attempted debenzoylation of the intermediate N-6,N-6,O-2'-tribenzoyladenosine cyclic 3',5'-phosphorofluoridate 4 by ammonolysis resulted in cleavage of the P-F bond. Reaction of [Sp]-S-methyl adenosine 3',5'-cyclophosphorothioate 6 with AgF gives a mixture of the two diastereoisomers of the cyclic phosphorofluoridate 7 along with adenosine 2',3'-cyclic phosphate 8. The conversion of 7 into 8 can be completed under remarkably mild conditions. Possible mechanisms for this unusual transformation are discussed.

  DOI：

  10.1016/0040-4039(95)01691-a
• 作为产物：
  描述：

  Sp isomer of adenosine 3′,5′-cyclic monophosphorothioate 、 碘甲烷 以 甲醇 、 苯 为溶剂， 反应 3.0h， 生成 -S-methyl adenosine 3',5'-cyclophosphorothioate
  参考文献：
  名称：

  Synthesis of adenosine cyclic 3ȃ,5ȃ-phosphorof)uoridate (camp-f)

  摘要：

  Work aimed at the chiral synthesis of both diastereomers of adenosine cyclic 3',5'-phosphorofluoridate, cAMP-F 7, is described. Attempted debenzoylation of the intermediate N-6,N-6,O-2'-tribenzoyladenosine cyclic 3',5'-phosphorofluoridate 4 by ammonolysis resulted in cleavage of the P-F bond. Reaction of [Sp]-S-methyl adenosine 3',5'-cyclophosphorothioate 6 with AgF gives a mixture of the two diastereoisomers of the cyclic phosphorofluoridate 7 along with adenosine 2',3'-cyclic phosphate 8. The conversion of 7 into 8 can be completed under remarkably mild conditions. Possible mechanisms for this unusual transformation are discussed.

  DOI：

  10.1016/0040-4039(95)01691-a