4(S)-(6-amino-9H-purin-9-yl)-2(S)-(O-benzoylmethyl)tetrahydrofuran | 151223-87-9

• 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: 4(S)-(6-amino-9H-purin-9-yl)-2(S)-(O-benzoylmethyl)tetrahydrofuran
• 英文别名: 4(S)-(6-amino-9H-purin-9-yl)tetrahydro-2(S)-furanmethanol benzoate；[(2S,4S)-4-(6-aminopurin-9-yl)oxolan-2-yl]methyl benzoate
• CAS: 151223-87-9
• 化学式: C₁₇H₁₇N₅O₃
• 分子量: 339.354
• InChiKey: UBPHGZPSSSLCDH-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  105.15
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  5-O-benzoyl-α-D-xylofuranose 在 吡啶 、 盐酸 、 三乙基硅烷 、 18-冠醚-6 、 偶氮二异丁腈 、 三氟甲磺酸三甲基硅酯 、 三正丁基氢锡 、 potassium carbonate 、 N,N'-硫羰基二咪唑 、 六甲基二硅氮烷 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 20.0h， 生成 4(S)-(6-amino-9H-purin-9-yl)-2(S)-(O-benzoylmethyl)tetrahydrofuran
  参考文献：
  名称：

  Zintek, Lawrence B.; Jeon, Geun Sook; Nair, Vasu, Heterocycles, 1994, vol. 37, # 3, p. 1853 - 1864

  摘要：

  DOI：

文献信息

• 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.
• Synthesis of Isomeric Dideoxynucleosides with Partial Symmetry
  作者：Vasu Nair、Lawrence Zintek、Geun Jeon

  DOI：10.1080/15257779508012391

  日期：1995.5.1

  Approaches to the synthesis of (S) and (R) enantiomers of hydroxymethylated isodideoxynucleosides have been developed. Because of the symmetry introduced at the carbon that normally bears the -CH2OH group, these compounds have only one asymmetric center and each enantiomeric series may be viewed as being both D- and L-related.