9-(α-L-5-hydroxymethyl-2-tetrahydrofuranyl)adenine | 121154-50-5

• 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: 9-(α-L-5-hydroxymethyl-2-tetrahydrofuranyl)adenine
• 英文别名: 6-amino-9-(α-L-2',3'-dideoxyribofuranosyl)purine；6-amino-9-(2,3-dideoxy-α-L-ribofuranosyl)purine；[(2R,5R)-5-(6-aminopurin-9-yl)tetrahydrofuran-2-yl]methanol；[(2R,5R)-5-(6-aminopurin-9-yl)oxolan-2-yl]methanol
• CAS: 121154-50-5
• 化学式: C₁₀H₁₃N₅O₂
• 分子量: 235.246
• InChiKey: WVXRAFOPTSTNLL-RNFRBKRXSA-N

物化性质

• 沸点：
  539.1±60.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  17
• 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：
  99.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-(α-L-5-hydroxymethyl-2-tetrahydrofuranyl)adenine 在 potassium phosphate buffer 、 adenosine deaminase 作用下， 反应 24.0h， 以47%的产率得到9-(α-L-2',3'-dideoxyribofuranosyl)hypoxanthine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Pyrimidine and Purine α-L-2′,3′-Dideoxy Nucleosides

  摘要：

  A series of alpha-L-2',3'-dideoxy nucleosides was prepared as potential antiviral agents. The pyrimidine nucleosides were prepared by standard Vorbruggen coupling reactions. The purine analogues were prepared by enzymatic transfer of the dideoxy sugar from a pyrimidine to a purine base. These compounds were inactive against HIV-1, HBV, HSV-I and -2, VZV, and HCMV.

  DOI：

  10.1080/15257779408009473
• 作为产物：
  描述：

  6-chloro-9-<5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-L-ribofuranosyl>purine 在 甲醇 、 四丁基氟化铵 、 氨 作用下， 以 四氢呋喃 为溶剂， 反应 73.0h， 生成 9-(α-L-5-hydroxymethyl-2-tetrahydrofuranyl)adenine
  参考文献：
  名称：

  Synthesis of a Series of Purine 2′,3′-Dideoxy-L-Nucleoside Analogues as Potential Antiviral Agents

  摘要：

  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.

  DOI：

  10.1080/15257779508009755

文献信息

• Identification of sugar degradation intermediates in a metalloporphyrin mediated DNA cleavage resulting from hydroxylation at C-5′
  作者：Geneviève Pratviel、Marguerite Pitié、Christian Périgaud、Gilles Gosselin、Jean Bernadou、Bernard Meunier

  DOI：10.1039/c39930000149

  日期：——

  Hydroxylation of poly(dA)·poly(dT) at the 5′ position of the deoxyribose units by the chemical nuclease Mn-TMPyP–KHSO5[Mn–TMPyP = manganese(III) complex of meso-tetrakis(4-N-methylpyridiniumyl)porphyrin] followed by an additional thermal step provides 5′-aldehyde-3′,4′-unsaturated nucleosides which can be reduced by sodium borohydride and then hydrogenated with palladium on charcoal giving 2′,3′-dideoxyribonucleosides having the natural β or the non-natural α configuration at 4′.

  化学核酸酶 Mn-TMPyPâKHSO5[MnâTMPyP=中-四(4-N-甲基吡啶鎓)卟啉的锰(III)络合物]在脱氧核糖单元的 5â²位对聚(dA)Â-聚(dT)进行羟基化，然后再经过一个热步骤，得到 5â²-醛-3â²、4â²-不饱和核苷，这种核苷可以用硼氢化钠还原，然后在炭上用钯氢化，得到 2â²,3â²-二脱氧核苷，这种核苷在 4â² 处具有天然的 β 或非天然的 α 构型。
• IKEHDA, TAKAO
  作者：IKEHDA, TAKAO

  DOI：——

  日期：——
• MANSURI, MUZAMMIL M.;FARINA, VITTORIO;STARRETT, JOHN E. (JR);BENIGNI, DAN+, BIOORG. AND MED. CHEM. LETT., 1,(1991) N, C. 65-68
  作者：MANSURI, MUZAMMIL M.、FARINA, VITTORIO、STARRETT, JOHN E. (JR)、BENIGNI, DAN+

  DOI：——

  日期：——
• 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.
• Synthesis and Biological Evaluation of Pyrimidine and Purine α-L-2′,3′-Dideoxy Nucleosides
  作者：Naina A. Van Draanen、George W. Koszalka

  DOI：10.1080/15257779408009473

  日期：1994.9

  A series of alpha-L-2',3'-dideoxy nucleosides was prepared as potential antiviral agents. The pyrimidine nucleosides were prepared by standard Vorbruggen coupling reactions. The purine analogues were prepared by enzymatic transfer of the dideoxy sugar from a pyrimidine to a purine base. These compounds were inactive against HIV-1, HBV, HSV-I and -2, VZV, and HCMV.