methyl 5-O-benzoyl-3-deoxy-D-erythro-pentofuranose | 143191-74-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 5-O-benzoyl-3-deoxy-D-erythro-pentofuranose
• CAS: 143191-74-6
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: LTRUBXMMBMQRKB-VUDPYIQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.97
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 5-O-benzoyl-3-deoxy-D-erythro-pentofuranose 在 吡啶 、 三乙基硅烷 、 18-冠醚-6 、 三氟甲磺酸三甲基硅酯 、 potassium carbonate 、 六甲基二硅氮烷 作用下， 以 N,N-二甲基甲酰胺 、 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：
• 作为产物：
  描述：

  5-O-benzoyl-3-O-(1-imidazolylthiocarbonyl)-1,2-O-isopropylidene-α-D-xylofuranose 在 盐酸 、 偶氮二异丁腈 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 14.0h， 生成 methyl 5-O-benzoyl-3-deoxy-D-erythro-pentofuranose
  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

• ISONUCLEOSIDES INCORPORATING UNIVERSAL BASES
  作者：Vasu Nair、David S. Sosnouski、Qingming Zhu

  DOI：10.1081/ncn-100002362

  日期：2001.3.31

  Enantiomeric isodideoxynucleosides of the (S,S) and (R,R) families with the universal base, imidazole-4-carboxamide as the nucleobase, were synthesized as biological mimics of anti-HIV active D- and L-related isodideo-xyadenosines. In vitro anti-HIV evaluation in CEM cells of these target compounds showed that they were inactive. Further antiviral studies are in progress.