(1S,2S,3R)-2,6-dichloro-9-(2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-yl)-9H-purine | 911701-28-5

• 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: (1S,2S,3R)-2,6-dichloro-9-(2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-yl)-9H-purine
• 英文别名: 9-[(3aS,4S,6aR)-2,2-dimethyl-3a,4,6,6a-tetrahydrothieno[3,4-d][1,3]dioxol-4-yl]-2,6-dichloropurine
• CAS: 911701-28-5
• 化学式: C₁₂H₁₂Cl₂N₄O₂S
• 分子量: 347.225
• InChiKey: VNNGNBXSVVCBID-AYKAFODUSA-N

物化性质

• 沸点：
  457.3±55.0 °C(Predicted)
• 密度：
  1.86±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  87.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R)-2,6-dichloro-9-(2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-yl)-9H-purine 在 盐酸 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 18.0h， 生成 9-[(2S,3S,4R)-3,4-Bis-(tetrahydro-pyran-2-yloxy)-tetrahydro-thiophen-2-yl]-2,6-dichloro-9H-purine
  参考文献：
  名称：

  Stereoselective Functionalization of the 1‘-Position of 4‘-Thionucleosides

  摘要：

  Stereoselective synthesis of novel 1'-alpha-substituted-4'-thionucleosides was achieved starting from D-gulonic acid gamma-lactone via stereoselective nucleophilic substitution.

  DOI：

  10.1021/ol061548z
• 作为产物：
  描述：

  (1R)-1-((3aS,4R,6aR)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-yl)-ethane-1,2-diol 在 ammonium sulfate 、 六甲基二硅氮烷 作用下， 以 乙酸乙酯 为溶剂， 反应 22.0h， 生成 (1S,2S,3R)-2,6-dichloro-9-(2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-yl)-9H-purine
  参考文献：
  名称：

  Stereoselective Functionalization of the 1‘-Position of 4‘-Thionucleosides

  摘要：

  Stereoselective synthesis of novel 1'-alpha-substituted-4'-thionucleosides was achieved starting from D-gulonic acid gamma-lactone via stereoselective nucleophilic substitution.

  DOI：

  10.1021/ol061548z

文献信息

• Stereoselective Synthesis of 1′-Functionalized-4′-Thionucleosides
  作者：Lak Shin Jeong、Prashantha Gunaga、Hea Ok Kim、Dilip K. Tosh、Hyuk Woo Lee、Seung Ah Choe、Hyung Ryong Moon、Zhan-Guo Gao、Kenneth A. Jacobson、Moon Woo Chun

  DOI：10.1080/15257770701508588

  日期：2007.11.26

  Stereoselective functionalization of the 1'-position of 4'-thionucleosides was achieved using a stereoselective S(N)2 reaction controlled by 5-membered ring coordination.
• Structure−Activity Relationships of Truncated <scp>d</scp>- and <scp>l</scp>-4′-Thioadenosine Derivatives as Species-Independent A₃ Adenosine Receptor Antagonists
  作者：Lak Shin Jeong、Shantanu Pal、Seung Ah Choe、Won Jun Choi、Kenneth A. Jacobson、Zhan-Guo Gao、Athena M. Klutz、Xiyan Hou、Hea Ok Kim、Hyuk Woo Lee、Sang Kook Lee、Dilip K. Tosh、Hyung Ryong Moon

  DOI：10.1021/jm8008647

  日期：2008.10.23

  Novel D- and L-4'-thioadenosine derivatives lacking the 4'-hydroxymethyl moiety were synthesized, starting from D-mannose and D-gulonic gamma-lactone, respectively, as potent and selective species-independent A(3) adenosine receptor (AR) antagonists. Among the novel 4'-truncated 2-H nucleosides tested, a N-6-(3-chlorobenzyl) derivative 7c was the most potent at the human A(3) AR (K-i = 1.5 nM), but a N-6-(3-bromobenzyl) derivative 7d showed the optimal species-independent binding affinity.
• Stereoselective Functionalization of the 1‘-Position of 4‘-Thionucleosides
  作者：Prashantha Gunaga、Hea Ok Kim、Hyuk Woo Lee、Dilip K. Tosh、Jae-Sang Ryu、Sun Choi、Lak Shin Jeong

  DOI：10.1021/ol061548z

  日期：2006.9

  Stereoselective synthesis of novel 1'-alpha-substituted-4'-thionucleosides was achieved starting from D-gulonic acid gamma-lactone via stereoselective nucleophilic substitution.