1,4-anhydro-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-D-ribitol | 143191-76-8

• 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: 1,4-anhydro-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-D-ribitol
• 英文别名: [(2S,4R)-4-(4-methylphenyl)sulfonyloxyoxolan-2-yl]methyl benzoate
• CAS: 143191-76-8
• 化学式: C₁₉H₂₀O₆S
• 分子量: 376.43
• InChiKey: PMKMQLSAABGZHI-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4-anhydro-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-D-ribitol 在 二氯乙酸 、 18-冠醚-6 、 sodium methylate 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 (2S,4S)-4-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde
  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：

  1,2:3,5-双-O-异亚丙基-alpha-D-呋喃木糖 在 吡啶 、 盐酸 、 三乙基硅烷 、 偶氮二异丁腈 、 三氟甲磺酸三甲基硅酯 、 三正丁基氢锡 、 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 、 甲苯 、 乙腈 为溶剂， 生成 1,4-anhydro-5-O-benzoyl-3-deoxy-2-O-p-toluenesulfonyl-D-ribitol
  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

• 2'isodideoxy-.beta.-D-nucleosides as stable antiviral agents
  申请人：University of Iowa Research Foundation

  公开号：US05231174A1

  公开（公告）日：1993-07-27

  The present invention is concerned wtih new 2'-isomeric 2 2',3'-dideoxy-2'.beta.-D-nucleosides and their derivatives where the base moiety has .beta.-stereochemistry but is transposed from the normal 1'-position to the 2'-position and the carbohydrate moiety has the D-configuration at the 4'-position. These compounds are resistant towards hydrolytic cleavage of the glycosidic bond and are resistant to enzymatic deamination. They have potential in the treatment or prophylaxis of viral infections, particularly retroviral infections and especially AIDS.

  本发明涉及新的2'-异构体2,2',3'-二去氧-2'.β.-D-核苷和它们的衍生物，其中碱基基团具有β-立体化学，但从正常的1'-位置转移到2'-位置，而碳水化合物基团在4'-位置具有D-构型。这些化合物对糖苷键的水解裂解具有抗性，并且对酶催化的脱氨基作用具有抗性。它们在治疗或预防病毒感染方面具有潜力，特别是对逆转录病毒感染，尤其是艾滋病具有潜在作用。
• Isodideoxynucleosides: a conceptually new class of nucleoside antiviral agents.
  作者：Vasu Nair、Zoraida M. Nuesca

  DOI：10.1021/ja00046a074

  日期：1992.9
• 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.
• Synthesis of New Dideoxynucleosides Bearing Ring-Extended Nucleobases
  作者：Jianzhong Zhang、Vasu Nair

  DOI：10.1080/07328319708006139

  日期：1997.7

  New dideoxynucleosides where the nucleobase is lin-benzoadenine is reported. The key target compound, (S, S)-isodideoxybenzoadenosine, is stable with respect to hydrolytic cleavage of the glycosyl bond and it is a poor substrate for adenosine deaminase. Its monophosphate is not a substrate for AMP deaminase.