(-)-9-[(3R,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-yl]-6-chloro-9H-purine | 917377-38-9

• 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: (-)-9-[(3R,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-yl]-6-chloro-9H-purine
• CAS: 917377-38-9
• 化学式: C₂₆H₂₈ClFN₄OSSi
• 分子量: 527.137
• InChiKey: BCOCIHBOBMCQEX-VSKRKVRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  52.83
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (-)-9-[(3R,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-yl]-6-chloro-9H-purine 在 氨 作用下， 以 甲醇 为溶剂， 以68%的产率得到[(2R,3S,4S)-4-(6-aminopurin-9-yl)-3-fluorothiolan-2-yl]methanol
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel iso-d-2′,3′-dideoxy-3′-fluorothianucleoside derivatives

  摘要：

  Novel iso-D-2',3'-dideoxythianucleoside derivatives 1-4 were designed and asymmetrically synthesized as a bioisostere of lamivudine to search for new anti-HIV agents. The information about using sulfur participation occurred on DAST fluorination and Mitsunobu reaction will be of great help in synthesizing sulfur-containing compounds. Final compounds 1-4 were evaluated against HIV-1 and 2, HSV-1 and 2, EMCV, Cox. B3, VSV, FluA (Taiwan), FluA (Johan.), FCV, and FIR Only cytosine analogue 3 showed a potent anti-VSV activity (EC50 = 9.43 mu g/mL). This result implies that iso-2',3'-dideoxy sugar templates might play a role of a sugar surrogate of nucleosides for the development of anti-RNA virus agent. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.066
• 作为产物：
  描述：

  (3S,4S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-phenylmethoxythiolan-3-ol 在 吡啶 、 4-二甲氨基吡啶 、 二乙胺基三氟化硫 、 sodium methylate 、 三氯化硼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 13.17h， 生成 (-)-9-[(3R,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-yl]-6-chloro-9H-purine
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel iso-d-2′,3′-dideoxy-3′-fluorothianucleoside derivatives

  摘要：

  Novel iso-D-2',3'-dideoxythianucleoside derivatives 1-4 were designed and asymmetrically synthesized as a bioisostere of lamivudine to search for new anti-HIV agents. The information about using sulfur participation occurred on DAST fluorination and Mitsunobu reaction will be of great help in synthesizing sulfur-containing compounds. Final compounds 1-4 were evaluated against HIV-1 and 2, HSV-1 and 2, EMCV, Cox. B3, VSV, FluA (Taiwan), FluA (Johan.), FCV, and FIR Only cytosine analogue 3 showed a potent anti-VSV activity (EC50 = 9.43 mu g/mL). This result implies that iso-2',3'-dideoxy sugar templates might play a role of a sugar surrogate of nucleosides for the development of anti-RNA virus agent. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.066