[(1'R,2'S)-2',3'-O-isopropylidenedioxy-3'-cyclopenten-1'-yl]-9-H-adenine | 263721-49-9

• 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: [(1'R,2'S)-2',3'-O-isopropylidenedioxy-3'-cyclopenten-1'-yl]-9-H-adenine
• 英文别名: 9-[(6R,6aS)-2,2-dimethyl-6,6a-dihydro-5H-cyclopenta[d][1,3]dioxol-6-yl]purin-6-amine
• CAS: 263721-49-9
• 化学式: C₁₃H₁₅N₅O₂
• 分子量: 273.294
• InChiKey: WREGHHZFPVCLRH-XCBNKYQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  88.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(1'R,2'S)-2',3'-O-isopropylidenedioxy-3'-cyclopenten-1'-yl]-9-H-adenine 在 三氟乙酸 作用下， 反应 0.25h， 以10%的产率得到9-[(1'R,2'S)-2'-hydroxy-3'-oxocyclopentan-1'-yl]-9-H-adenine
  参考文献：
  名称：

  Facile synthesis of 9-[(1′R,2′S)-2′-hydroxy-3′-oxocyclopentan-1′-yl]-9-H-adenine possessing inhibitory activity against human recombinant S-adenosyl-l-homocysteine hydrolase

  摘要：

  Treatment of 4'-O-methanesulfonyl-2',3'-O-isopropylideneoraisteromycin with KOBut gave the corresponding 3',4'-dehydro derivative, and subsequent deprotection resulted in the formation of 9-[(1'R,2'S)-2'-hydroxy-3'-oxocyclopentan-1'-yl]-9-H-adenine possessing inhibitory activity against human recombinant S-adenosyl-L homocysteine hydrolase (EC 3.3.1.1). In sharp contrast to KOBut, when lithium azide was adopted as a base, 9-[(1'R,2'S,3'R)-2',3'-O-isopropylidened ioxy-4'-cyclopenten-1'-yl]-H-adenine was selectively obtained, and subsequent deprotection afforded DHCeA, which is a well-known potential antiviral agent. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01978-x
• 作为产物：
  描述：

  (-)-β-(4'β-hydroxy-2'α,3'α-O-isopropylidenedioxycyclopent-1'-yl)-9-H-adenine 在 4-二甲氨基吡啶 、 potassium tert-butylate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 [(1'R,2'S)-2',3'-O-isopropylidenedioxy-3'-cyclopenten-1'-yl]-9-H-adenine
  参考文献：
  名称：

  Facile synthesis of 9-[(1′R,2′S)-2′-hydroxy-3′-oxocyclopentan-1′-yl]-9-H-adenine possessing inhibitory activity against human recombinant S-adenosyl-l-homocysteine hydrolase

  摘要：

  Treatment of 4'-O-methanesulfonyl-2',3'-O-isopropylideneoraisteromycin with KOBut gave the corresponding 3',4'-dehydro derivative, and subsequent deprotection resulted in the formation of 9-[(1'R,2'S)-2'-hydroxy-3'-oxocyclopentan-1'-yl]-9-H-adenine possessing inhibitory activity against human recombinant S-adenosyl-L homocysteine hydrolase (EC 3.3.1.1). In sharp contrast to KOBut, when lithium azide was adopted as a base, 9-[(1'R,2'S,3'R)-2',3'-O-isopropylidened ioxy-4'-cyclopenten-1'-yl]-H-adenine was selectively obtained, and subsequent deprotection afforded DHCeA, which is a well-known potential antiviral agent. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01978-x