(2R,3R,4R,5R)-2-(6-Amino-purin-9-yl)-3,5-bis-benzyloxymethyl-tetrahydro-furan-3,4-diol | 908836-39-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: (2R,3R,4R,5R)-2-(6-Amino-purin-9-yl)-3,5-bis-benzyloxymethyl-tetrahydro-furan-3,4-diol
• CAS: 908836-39-5
• 化学式: C₂₅H₂₇N₅O₅
• 分子量: 477.52
• InChiKey: JZIJTOHWDJVZKY-GLOVNJMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  137.77
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-2-(6-Amino-purin-9-yl)-3,5-bis-benzyloxymethyl-tetrahydro-furan-3,4-diol 在 钯 甲酸 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以61%的产率得到2'-c-Hydroxymethyladenosine
  参考文献：
  名称：

  Synthesis of 2-C-hydroxymethylribofuranosylpurines as potent anti-hepatitis C virus (HCV) agents

  摘要：

  On the basis of potent anti-HCV activity of 2'-C-methyladenosine, novel 2'-C-hydroxymethyladenosine analogues 2a-c were synthesized from D-ribose in order to lead to favorable interaction with HCV polymerase. Among compounds tested, adenosine derivative 2a exhibited potent anti-HCV activity, indicating that the hydroxyl group of 2'-C-hydroxymethyl substituent led to favorable interaction with HCV polymerase. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.089
• 作为产物：
  描述：

  Acetic acid (2R,3R,4R,5R)-4-acetoxy-3,5-bis-benzyloxymethyl-2-(6-chloro-purin-9-yl)-tetrahydro-furan-3-yl ester 在 氨 作用下， 以 甲醇 为溶剂， 反应 25.0h， 生成 (2R,3R,4R,5R)-2-(6-Amino-purin-9-yl)-3,5-bis-benzyloxymethyl-tetrahydro-furan-3,4-diol
  参考文献：
  名称：

  Synthesis of 2-C-hydroxymethylribofuranosylpurines as potent anti-hepatitis C virus (HCV) agents

  摘要：

  On the basis of potent anti-HCV activity of 2'-C-methyladenosine, novel 2'-C-hydroxymethyladenosine analogues 2a-c were synthesized from D-ribose in order to lead to favorable interaction with HCV polymerase. Among compounds tested, adenosine derivative 2a exhibited potent anti-HCV activity, indicating that the hydroxyl group of 2'-C-hydroxymethyl substituent led to favorable interaction with HCV polymerase. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.089

文献信息

• Synthesis And Anti-Hcv Activity Of 2″-β-Hydroxymethylated Nucleosides
  作者：Lak Shin Jeong、Byul Nae Yoo、Hea Ok Kim、Kang Man Lee、Hyung Ryong Moon

  DOI：10.1080/15257770701493310

  日期：2007.11.26

  Synthesis of 2'-beta-hydroxymethyl nucleosides 3-6 was accomplished, using stereoselective hydroxymethylation as a key step. Adenine nucleoside 3 showed potent anti-HCV activity, implying that 2'-beta-hydroxymethylgroup has the appropriate electronic properties interfering with HCV polymerase.