Sp isomer of adenosine 3′,5′-cyclic monophosphorothioate

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: Sp isomer of adenosine 3′,5′-cyclic monophosphorothioate
• 英文别名: -adenosine cyclic 3',5'-phosphorothioate；(S)-adenosine-3',5'-cyclic monophosphorothioate；Sp-3',5'-cyclic adenosine monophosphorothioate；Sp-adenosine 3',5'-cyclic monophosphorothioate；adenosine 3',5'-cyclic monophosphothionate；(Sp)-adenosine-3',5'-cyclic monophosphorothioate
• 化学式: C₁₀H₁₂N₅O₅PS
• 分子量: 345.276
• InChiKey: SMPNJFHAPJOHPP-LHKKBNDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.12
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  134.61
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Sp isomer of adenosine 3′,5′-cyclic monophosphorothioate 在 吡啶 、 silver fluoride 作用下， 以 吡啶 、 甲醇 、 乙腈 、 苯 为溶剂， 反应 6.0h， 生成 腺苷-2’,3’-环磷酸
  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：

  N⁶,N⁶,O^2'-tribenzoyladenosine cyclic 3',5'-phosphoranilidate (R(P)) 生成 Sp isomer of adenosine 3′,5′-cyclic monophosphorothioate
  参考文献：
  名称：

  BARANIAK, JANINA;STEC, WOJCIECH J., J. CHEM. SOC. PERKIN TRANS., 1,(1987) N 8, 1645-1656

  摘要：

  DOI：

文献信息

• [EN] PURINE NUCLEOTIDE DERIVATIVES<br/>[FR] DERIVES DE NUCLEOTIDE PURIQUE
  申请人：LAURAS AS

  公开号：WO2005123755A3

  公开（公告）日：2006-04-06
• BARANIAK, JANINA;STEC, WOJCIECH J., J. CHEM. SOC. PERKIN TRANS., 1,(1987) N 8, 1645-1656
  作者：BARANIAK, JANINA、STEC, WOJCIECH J.

  DOI：——

  日期：——
• GENLESER, HANS-GOTTFRIED;DOSTMANN, WOLFGANG;BOTTIN, ULRIKE;BUTT, ELKE;JAS+, TETRAHEDRON LETT., 29,(1988) N 23, 2803-2804
  作者：GENLESER, HANS-GOTTFRIED、DOSTMANN, WOLFGANG、BOTTIN, ULRIKE、BUTT, ELKE、JAS+

  DOI：——

  日期：——
• Synthesis of adenosine cyclic 3ȃ,5ȃ-phosphorof)uoridate (camp-f)
  作者：Janina Baraniak、Wojciech J. Stec、G. Michael Blackburn

  DOI：10.1016/0040-4039(95)01691-a

  日期：1995.10

  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.