N⁶-benzoyl-α-2'-deoxy-3',5'-di-O-p-toluoyladenosine | 146039-01-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N⁶-benzoyl-α-2'-deoxy-3',5'-di-O-p-toluoyladenosine
• 英文别名: [(2R,3S,5S)-5-(6-benzamidopurin-9-yl)-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 146039-01-2
• 化学式: C₃₃H₂₉N₅O₆
• 分子量: 591.623
• InChiKey: PSLFODKRCXLIGC-VJGNERBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1-Α-氯-3,5-二-O-对甲苯甲酰基-2-脱氧-D-呋喃核糖 、 N6-benzoyladenine sodium salt 生成 N⁶-benzoyl-β-2'-deoxy-3',5'-di-O-p-toluoyladenosine 、 N⁶-benzoyl-α-2'-deoxy-3',5'-di-O-p-toluoyladenosine
  参考文献：
  名称：

  Facile Stereospecific Synthesis of a-Anomeric 2'-Deoxynucleosides

  摘要：

  The coupling reaction of activated nucleobases, such as the sodium salts of N-benzoyladenine and 6-chloropurine and 2,4-bis-O-trimethylsilylthymine, with 1-alpha-chloro-2-deoxy-3,5-di-O-p-toluoylribofuranose (1) in a mixture of acetonitrile and tetrahydrufuran leads to the stereospecific formation of a-anomeric 2'-deoxynucleosides with satisfactory yields. The ratio of the distribution between the resulted alpha- and beta-stereoisomers was about 3:1 in each case. The method is simple and applicable to the preparation of both purine and pyrimidine alpha-2'-deoxynucleosides.

  DOI：

  10.3987/com-92-6125

文献信息

• Investigation of stereoselectivities in the coupling reactions of 1-O-methyl-3, 5-di-O-p-toluoyl-2-deoxyribofuranoside with purines and pyrimidines
  作者：Selvasekaran Janardhanam、Krishnan P. Nambiar

  DOI：10.1016/s0040-4039(00)73064-4

  日期：1994.5

  Stereoselectivities in the coupling reaction between 1-O-methyl-3,5-di-O-p-toluoyl-2-deoxyribofuranoside and suitably protected purine and pyrimidine derivatives have been examined in acetonitrile with varying equivalents of SnCl4. The best result in alpha-nucleoside formation was obtained when the coupling reaction was carried out in the presence of ten equivalents of SnCl4.
• Facile Stereospecific Synthesis of a-Anomeric 2'-Deoxynucleosides
  作者：Kazuo Shinozuka、Yoshiki Hirota、Tsutomu Morita、Hiroaki Sawai

  DOI：10.3987/com-92-6125

  日期：——

  The coupling reaction of activated nucleobases, such as the sodium salts of N-benzoyladenine and 6-chloropurine and 2,4-bis-O-trimethylsilylthymine, with 1-alpha-chloro-2-deoxy-3,5-di-O-p-toluoylribofuranose (1) in a mixture of acetonitrile and tetrahydrufuran leads to the stereospecific formation of a-anomeric 2'-deoxynucleosides with satisfactory yields. The ratio of the distribution between the resulted alpha- and beta-stereoisomers was about 3:1 in each case. The method is simple and applicable to the preparation of both purine and pyrimidine alpha-2'-deoxynucleosides.