Hexadecanoic acid (9-trimethylsilanyl-6-trimethylsilanyloxy-9H-purin-2-yl)-amide | 91703-93-4

• 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: Hexadecanoic acid (9-trimethylsilanyl-6-trimethylsilanyloxy-9H-purin-2-yl)-amide
• 英文别名: N-(9-trimethylsilyl-6-trimethylsilyloxypurin-2-yl)hexadecanamide
• CAS: 91703-93-4
• 化学式: C₂₇H₅₁N₅O₂Si₂
• 分子量: 533.905
• InChiKey: YVFHISKWCZMLQU-UHFFFAOYSA-N

物化性质

• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.14
• 重原子数：
  36.0
• 可旋转键数：
  18.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  81.93
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Hexadecanoic acid (9-trimethylsilanyl-6-trimethylsilanyloxy-9H-purin-2-yl)-amide 在 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.0h， 生成 9-(2,3-dideoxy-α-L-ribofuranosyl)-2-palmitoylguanine
  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
• 作为产物：
  描述：

  鸟嘌呤 以 吡啶 为溶剂， 反应 12.17h， 生成 Hexadecanoic acid (9-trimethylsilanyl-6-trimethylsilanyloxy-9H-purin-2-yl)-amide
  参考文献：
  名称：

  Visser, G. M.; van Westrenen, J.; van Boeckel, C. A. A., Recueil des Travaux Chimiques des Pays-Bas, 1986, vol. 105, p. 528 - 537

  摘要：

  DOI：

文献信息

• Visser, G. M; Westrenen, J. van; Boeckel, C. A. A. van, Recueil des Travaux Chimiques des Pays-Bas, 1984, vol. 103, # 4, p. 141 - 142
  作者：Visser, G. M、Westrenen, J. van、Boeckel, C. A. A. van、Boom, J. H. van

  DOI：——

  日期：——
• BEJGELMAN, L. N.;MIXAJLOV, S. N., DOKL. AN CCCP, 296,(1987) N 6, 1379-1382
  作者：BEJGELMAN, L. N.、MIXAJLOV, S. N.

  DOI：——

  日期：——