Methanesulfonic acid (R)-1-[(4S,5S)-5-(6-amino-purin-9-ylmethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-methanesulfonyloxy-ethyl ester | 212755-97-0

• 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: Methanesulfonic acid (R)-1-[(4S,5S)-5-(6-amino-purin-9-ylmethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-methanesulfonyloxy-ethyl ester
• 英文别名: [(2R)-2-[(4S,5S)-5-[(6-aminopurin-9-yl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methylsulfonyloxyethyl] methanesulfonate
• CAS: 212755-97-0
• 化学式: C₁₅H₂₃N₅O₈S₂
• 分子量: 465.508
• InChiKey: FYYGWARHGUGGFH-UMNHJUIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  192
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (R)-1-[(4S,5S)-5-(6-amino-purin-9-ylmethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-methanesulfonyloxy-ethyl ester 在 溶剂黄146 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 13.5h， 生成 9-((2S,3R)-2,3-dihydroxy-4-penten-1-yl)adenine
  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：

  甲基磺酰氯 、 9-[(2S,3R,4R)-(5,4-dihydroxy-2,3-isopropylidenedioxy)pentyl]adenine 在 吡啶 作用下， 生成 Methanesulfonic acid (R)-1-[(4S,5S)-5-(6-amino-purin-9-ylmethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-methanesulfonyloxy-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

文献信息

• 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.