9-(2,3-dideoxy-β-L-ribofuranosyl)guanine | 160962-93-6

• 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: 9-(2,3-dideoxy-β-L-ribofuranosyl)guanine
• 英文别名: β-L-d2G；β-L-2',3'-dideoxyguanosine；2-amino-9-[(2S,5R)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-purin-6-one；2-amino-9-[(2S,5R)-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 160962-93-6
• 化学式: C₁₀H₁₃N₅O₃
• 分子量: 251.245
• InChiKey: OCLZPNCLRLDXJC-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-L-erythro-pentonic acid-γ-lactone 在 4-二甲氨基吡啶 、 三乙基硼 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 氨 、 三正丁基氢锡 、 sodium methylate 、 二异丁基氢化铝 、 2-巯基乙醇 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 苯 为溶剂， 反应 2.0h， 生成 9-(2,3-dideoxy-β-L-ribofuranosyl)guanine
  参考文献：
  名称：

  Anti-human immunodeficiency and anti-hepatitis B virus activities of β-l-2′,3′-dideoxy purine nucleosides

  摘要：

  beta-L-2',3'-Dideoxyadenosine, beta-L-2',3'-didehydro-2',3'-dideoxyadenosine and related compounds were synthesized in a stereoselective manner. These compounds were tested in vitro against HBV in 2.2.15 cell line and against HIV-1 in PBM and CEM cells. It was found that beta-L-2',3'-didehydro-2',3'-dideoxyadenosine (7) exhibited significant anti-HIV (EC(50) 0.38 mu M in PBM cells) and anti-HBV activity (EC(50) 1.2 mu M). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00293-4

文献信息

• Synthesis of a Series of Purine 2′,3′-Dideoxy-L-Nucleoside Analogues as Potential Antiviral Agents
  作者：Tai-Shun Lin、Mei-Zhen Luo、Ju-Liang Zhu、Mao-Chin Liu、Yong-Lian Zhu、Ginger E. Dutschman、Yung-Chi Cheng

  DOI：10.1080/15257779508009755

  日期：1995.10

  Various 2',3'-dideoxy-L-nucleoside analogues, 6-amino-9-(2,3-dideoxy-beta-L-ribofuranosy))purine (19), 2-chloro-6-amino-9-(2,3-dideoxy-beta-L-ribofuranosyl)-purine (20), 2-chloro-6-amino-9-(2,3-dideoxy-4-thio-beta-L-ribofuranosyl)purine (21), 2,5- diamino 9-(2,3-dideoxy-beta-L-ribofuranosyl)purine (26), 2,6-diamino-9-(2,3-dideoxy-4-thio-beta-L-ribofuranosyl)-purine (27), 2-amino-6-chloro-9-(2,3-dideoxy-beta-L-ribofuranosyl)purine (28), (6-chloro-9-(2,3-dideoxy-4-thio-beta-L-ribofuranosyl)purine (29), and 6-amino-9-(2,3-dideoxy-4-thio-beta-L-ribofuranosyl)purine (30) have been synthesized by coupling of the sodium salt of 2-amino-6-chloropurine (1), 6-chloropurine (2), and 2,6-dichloropurine urine (3) with 1-O-acetyl-5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-L-ribofuranose (4) or 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-4-thio-L-ribofuranose (5) in anhydrous MeCN in the presence of either EtAlCl(2) or Et(2)AlCl followed by separation of the alp-anomers and deprotection of the blocking groups. However, the synthesis of 9-(2,3-dideoxy-beta-L-ribofuranosyl)guanine (57, beta-L-ddG) was not straightforward. Coupling of the silylated N-2-palmitoylguanine (48) with sugar 4 in anhydrous MeCN, using trimethylsilyl trifluoromethanesulfonate as a catalyst yielded N-9-beta- and N-9-alpha-; N-7-beta- and N-7-alpha-isomers, compounds 49-52, which were separated by silica gel column chromatography with two appropriate eluting solvent systems. Removal of the protecting groups gave compound 57 (beta-L-ddC) and the other 3 related isomers (58-60). The 2',3'-dideoxy-L-nucleoside analogues were tested in vitro against HIV-1, HBV, L1210, P388, S-180, and CCRF-CEM. 6-Amino-9-(2,3-dideoxy-beta-L-ribofuranosyl)purine (19, beta-L-ddA) was found to have antiviral activity against HBV with an ED(50) value of 6 mu M.
• Anti-human immunodeficiency and anti-hepatitis B virus activities of β-l-2′,3′-dideoxy purine nucleosides
  作者：Pascal J. Bolon、Peiyuan Wang、Chung K. Chu、Gilles Gosselin、Valérie Boudou、Claire Pierra、Christophe Mathé、Jean-Louis Imbach、Abdesselem Faraj、Abdelaziz el Alaoui、Jean-Pierre Sommadossi、S.Balakrishna Pai、Yong-Lian Zhu、Ju-Sheng Lin、Yung-Chi Cheng、Raymond F. Schinazi

  DOI：10.1016/0960-894x(96)00293-4

  日期：1996.7

  beta-L-2',3'-Dideoxyadenosine, beta-L-2',3'-didehydro-2',3'-dideoxyadenosine and related compounds were synthesized in a stereoselective manner. These compounds were tested in vitro against HBV in 2.2.15 cell line and against HIV-1 in PBM and CEM cells. It was found that beta-L-2',3'-didehydro-2',3'-dideoxyadenosine (7) exhibited significant anti-HIV (EC(50) 0.38 mu M in PBM cells) and anti-HBV activity (EC(50) 1.2 mu M). Copyright (C) 1996 Elsevier Science Ltd
• Stereoselective Synthesis of β-L-2′, 3′-Dideoxy-and L-2′,3′-Didehydro-2′,3′-Dideoxy Purine Nucleosides
  作者：Peiyuan Wang、Pascal J. Bolon、M. Gary Newton、Chung K. Chua

  DOI：10.1080/07328319908044642

  日期：1999.11

  beta-L-2',3'-Dideoxy- and L-2',3'-didehydro-2',3'-dideoxy purine nucleosides have been synthesized via a highly stereoselective method of glycosylation by the condensation of L-2-(phenylselenyl)-2,3-dideoxyribose derivative with silylated heterocyclic base.