2-Amino-9-[(2S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dihydro-furan-2-yl]-9H-purin-6-ol | 259256-63-8

• 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: 2-Amino-9-[(2S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dihydro-furan-2-yl]-9H-purin-6-ol
• 英文别名: 2-Amino-9-[(2S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dihydro-furan-2-yl]-1,9-dihydro-purin-6-one
• CAS: 259256-63-8
• 化学式: C₂₆H₂₉N₅O₃Si
• 分子量: 487.633
• InChiKey: SYWJXGYGURGVFM-NQIIRXRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 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：
  0.27
• 拓扑面积：
  108.31
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-Amino-9-[(2S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dihydro-furan-2-yl]-9H-purin-6-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 9-(2,3-dideoxy-β-L-glycero-pent-2-enofuranosyl)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
• 作为产物：
  描述：

  1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-α-and-β-L-erythro-pentofuranose 在 三氟甲磺酸三甲基硅酯 、 氨 、 双氧水 、 sodium methylate 、 2-巯基乙醇 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 2.0h， 生成 2-Amino-9-[(2S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dihydro-furan-2-yl]-9H-purin-6-ol
  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

• 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.