2(S)-(O-acetylmethyl)-4(S)-(6-amino-9H-purin-9-yl)tetrahydrofuran | 151223-85-7

• 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(S)-(O-acetylmethyl)-4(S)-(6-amino-9H-purin-9-yl)tetrahydrofuran
• 英文别名: [(2S,4S)-4-(6-aminopurin-9-yl)tetrahydrofuran-2-yl]methyl acetate；[(2S,4S)-4-(6-aminopurin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 151223-85-7
• 化学式: C₁₂H₁₅N₅O₃
• 分子量: 277.283
• InChiKey: OYTXWBMKLIINSP-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2(S)-(O-acetylmethyl)-4(S)-(6-amino-9H-purin-9-yl)tetrahydrofuran 在 亚硝酸正戊酯 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以55.4%的产率得到4(S)-(9H-purin-9-yl)tetrahydro-2(S)-furanmethylacetate
  参考文献：
  名称：

  Synthesis and Conformational Studies of New Purine Isodideoxynucleosides

  摘要：

  The synthesis and NMR conformational correlations (preferred syn or anti) of new isomeric dideoxynucleosides of potential antiviral interest are described. These compounds are related to the potently active anti-HIV compound, (S,S)-isodideoxy-adenosine.

  DOI：

  10.1080/07328319608002371
• 作为产物：
  描述：

  4(S)-(6-amino-9H-purin-9-yl)-2(S)-(O-benzoylmethyl)tetrahydrofuran 在 4-二甲氨基吡啶 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.38h， 生成 2(S)-(O-acetylmethyl)-4(S)-(6-amino-9H-purin-9-yl)tetrahydrofuran
  参考文献：
  名称：

  Novel isomeric dideoxynucleosides as potential antiviral agents

  摘要：

  Novel isomeric dideoxynucleosides with S,S absolute stereochemistry and involving the transposition of the base moiety from the normal 1'- to the 2'-position have been regiospecifically and stereospecifically synthesized. The synthetic approaches involved either direct coupling with inversion at the 2-position of a preformed dideoxygenated sugar using the base moiety as nucleophile (for purine isodideoxynucleosides) or construction of the base moiety onto a stereochemically defined amino sugar precursor (pyrimidine isodideoxynucleosides). These compounds possess extremely high stability with respect to ''glycosidic'' bond cleavage and enzymatic deamination. Antiviral data suggest that the most active compound was levorotatory S,S-isodideoxyadenosine.

  DOI：

  10.1016/s0040-4020(01)85259-5

文献信息

• US5231174A
  申请人：——

  公开号：US5231174A

  公开（公告）日：1993-07-27
• Novel isomeric dideoxynucleosides as potential antiviral agents
  作者：Pascal J. Bolon、Todd B. Sells、Zoraida M. Nuesca、David F. Purdy、Vasu Nair

  DOI：10.1016/s0040-4020(01)85259-5

  日期：1994.1

  Novel isomeric dideoxynucleosides with S,S absolute stereochemistry and involving the transposition of the base moiety from the normal 1'- to the 2'-position have been regiospecifically and stereospecifically synthesized. The synthetic approaches involved either direct coupling with inversion at the 2-position of a preformed dideoxygenated sugar using the base moiety as nucleophile (for purine isodideoxynucleosides) or construction of the base moiety onto a stereochemically defined amino sugar precursor (pyrimidine isodideoxynucleosides). These compounds possess extremely high stability with respect to ''glycosidic'' bond cleavage and enzymatic deamination. Antiviral data suggest that the most active compound was levorotatory S,S-isodideoxyadenosine.
• Synthesis and Conformational Studies of New Purine Isodideoxynucleosides
  作者：Lawrence B. Zintek、Tamera S. Jahnke、Vasu Nair

  DOI：10.1080/07328319608002371

  日期：1996.1

  The synthesis and NMR conformational correlations (preferred syn or anti) of new isomeric dideoxynucleosides of potential antiviral interest are described. These compounds are related to the potently active anti-HIV compound, (S,S)-isodideoxy-adenosine.