(E)-(4R,5S)-6-(6-Amino-purin-9-yl)-4,5-dihydroxy-hex-2-enoic acid ethyl ester | 212755-98-1

• 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: (E)-(4R,5S)-6-(6-Amino-purin-9-yl)-4,5-dihydroxy-hex-2-enoic acid ethyl ester
• 英文别名: ethyl (E,4R,5S)-6-(6-aminopurin-9-yl)-4,5-dihydroxyhex-2-enoate
• CAS: 212755-98-1
• 化学式: C₁₃H₁₇N₅O₄
• 分子量: 307.309
• InChiKey: CVXJAOFOZQAFQG-BKIAHZASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E)-(4R,5S)-6-(6-Amino-purin-9-yl)-4,5-dihydroxy-hex-2-enoic acid ethyl ester 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 11.0h， 以89%的产率得到(E)-(4R,5S)-6-(6-Amino-purin-9-yl)-4,5-dihydroxy-hex-2-enoic acid
  参考文献：
  名称：

  A Convenient Synthesis of Acyclic Adenosines with an Unsaturated Side Chain by Modification of 9-(2,3-O-Isopropylidene-D-Ribityl)Adenine

  摘要：

  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.

  DOI：

  10.1080/07328319808003472
• 作为产物：
  描述：

  (E)-3-[(4R,5S)-5-(6-Amino-purin-9-ylmethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acrylic acid ethyl ester 在 三氟乙酸 作用下， 反应 4.0h， 以83%的产率得到(E)-(4R,5S)-6-(6-Amino-purin-9-yl)-4,5-dihydroxy-hex-2-enoic acid ethyl ester
  参考文献：
  名称：

  A Convenient Synthesis of Acyclic Adenosines with an Unsaturated Side Chain by Modification of 9-(2,3-O-Isopropylidene-D-Ribityl)Adenine

  摘要：

  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.

  DOI：

  10.1080/07328319808003472