9-((2S,3R)-2,3-dihydroxy-4-penten-1-yl)adenine | 123619-95-4

• 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-((2S,3R)-2,3-dihydroxy-4-penten-1-yl)adenine
• 英文别名: (2S,3R)-1-(6-aminopurin-9-yl)pent-4-ene-2,3-diol
• CAS: 123619-95-4
• 化学式: C₁₀H₁₃N₅O₂
• 分子量: 235.246
• InChiKey: XTXOGYDRWAHTJV-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2S,3R)-2,3-isopropylidenedioxy-1-mesyloxy-4-pentene 在 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 9-((2S,3R)-2,3-dihydroxy-4-penten-1-yl)adenine
  参考文献：
  名称：

  Regiocontrol in the synthesis of optically active amino-4-pentenediols via epoxy-4-pentenols. Novel acyclic adenosine analogues

  摘要：

  DOI：

  10.1016/s0040-4039(00)99506-6

文献信息

• Regiocontrol in the synthesis of optically active amino-4-pentenediols via epoxy-4-pentenols. Novel acyclic adenosine analogues
  作者：Walter Hümmer、Tibor Gracza、Volker Jäger

  DOI：10.1016/s0040-4039(00)99506-6

  日期：1989.1
• A Convenient Synthesis of Acyclic Adenosines with an Unsaturated Side Chain by Modification of 9-(2,3-<i>O</i>-Isopropylidene-D-Ribityl)Adenine
  作者：Kosaku Hirota、Yasunari Monguchi、Hironao Sajiki、Chizuko Yatome、Akio Hiraoka、Yukio Kitade

  DOI：10.1080/07328319808003472

  日期：1998.8

  In expectation of discovering their antiviral activity, acyclic adenosine derivatives 7, 11, 12, and 16 were designed as analogs of neplanocin A (NPA) and L-eritadenine which are strong inhibitors of S-adenosyl-L-homocysteine hydrolase. The 1',5'-seco-analog of 4'-deoxymethyl-NPA (DHCA) 7 was synthesized by dideoxygenation of 9-(2, 3-O-isopropylidene-D-ribityl)adenine (2). Acyclic DHCA analogs 11 and 16 were obtained by Wittig reaction of the aldehyde 3 with Ph3P=CHCO2Et and Ph3P=CHCN, respectively. Hydrolysis of the ester 11 afforded a vinylog of L-eritadenine 12. The synthesized acyclic nucleosides 7, 10, and 11 were evaluated for antiviral activity, however, none of them showed any significant antiviral activity.
• HUMMER, WALTER;GRACZA, TIBOR;JAGER, VOLKER, TETRAHEDRON LETT., 30,(1989) N2, C. 1517-1520
  作者：HUMMER, WALTER、GRACZA, TIBOR、JAGER, VOLKER

  DOI：——

  日期：——
• Jaeger, Volker; Huemmer, Walter; Stahl, Ulrich, Synthesis, 1991, # 9, p. 769 - 776
  作者：Jaeger, Volker、Huemmer, Walter、Stahl, Ulrich、Gracza, Tibor

  DOI：——

  日期：——