3,5-O-二甲苯甲酰6-氯嘌呤-7-beta-D-脱氧核糖甙 | 91713-51-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 中文名称: 3,5-O-二甲苯甲酰6-氯嘌呤-7-beta-D-脱氧核糖甙
• 英文名称: 6-chloro-7-<2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-7H-purine
• 英文别名: 6-Chloro-7-(2'-deoxy-3',5'-di-O-p-toluyl-β-D-erythro-pentofuranosyl)purine；6-Chloro-7-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)purine；6-chloro-7-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythropentofuranosyl)purine；3,5-O-Ditoluoyl 6-Chloropurine-7-|A-D-deoxyriboside；[(2R,3S,5R)-5-(6-chloropurin-7-yl)-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 91713-51-8
• 化学式: C₂₆H₂₃ClN₄O₅
• 分子量: 506.945
• InChiKey: HNNXWQNWNACXEE-PWRODBHTSA-N

物化性质

• 熔点：
  152-153 °C
• 沸点：
  684.5±65.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、可溶于二氯甲烷、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,5-O-二甲苯甲酰6-氯嘌呤-7-beta-D-脱氧核糖甙 在 palladium on activated charcoal 氨 、 氢气 、 三乙胺 作用下， 生成 7-<2-deoxy-β-D-erythro-pentofuranosyl>-7H-purine
  参考文献：
  名称：

  Synthesis of 6-Substituted Purine N⁷-(2-Deoxy-β-D-Ribonucleosides) via Anion Glycosylation and Anomerization During the N⁷/N⁹-Glycosyl Transfer

  摘要：

  The synthesis of the 7-(2-deoxy-beta-D-erythro-pentofuranosyl) adenine (Ib) as well as the corresponding hypoxanthine- and purine nucleosides 3 and 4 is described employing the stereoselective nucleobase anion glycosylation. The N-7/N-9- isomer distribution of the 6-substituted purine (2-deoxyribonucleosides) depends on 6-substituent. Glycosyl transfer of 8a resulted in anomerization and yielded a mixture of the anomeric 6-methoxypurine N-9-(2-deoxy-D-ribonucleosides) 7a/7d. The preferred glycosylic bond conformation of purine N-7-(2-deoxyribonucleosides) is anti.

  DOI：

  10.1080/15257779508014658
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 iodonium di(2,4,6-trimethylpyridine) perchlorate 吡啶 、 4 A molecular sieve 、 camphor-10-sulfonic acid 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 3,5-O-二甲苯甲酰6-氯嘌呤-7-beta-D-脱氧核糖甙
  参考文献：
  名称：

  Pentenyl ribosides: new reagents for purine nucleoside synthesis

  摘要：

  Protected pent-4-enyl ribosides and deoxyribosides were synthesized as reagents for the preparation of nucleosides and deoxynucleosides. Reaction of pent-4-enyl 2',3',5'-tri-O-benzoyl-D-erythro-pentofuranoside with five nucleobases in the presence of N-iodosuccinimide/trifluoromethanesulfonic acid (NIS/TfOH) produced the N-9-beta-nucleosides in 50-70% yields. Pent-4-enyl-2-deoxy-3',5'-di-O-p-toluyl-alpha-D-erythro-pentofuranoside coupled with 6-chloropurine in the presence of iodonium dicollidine perchlorate (IDCP) to produce a mixture of deoxynucleoside isomers (N-9, N-7, alpha,beta) in 91% yield. Under the same conditions, coupling of 6-chloropurine with pent-4-enyl 2'-deoxy-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-D-erythro-pentofuranoside produced only N-9alpha and N-9beta products in 40% total yield. The N-9beta nucleoside was the only product of the reaction of 6-chloropurine with pent-4-enyl 2'-O-benzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-D-erythro-pentofuranoside in the presence of NIS/TfOH. Pent-4-enyl ribosides appear to be useful reagents for the synthesis of ribo- and deoxyribonucleosides under mild (NIS/TfOH) or neutral (IDCP) conditions.

  DOI：

  10.1021/jo00077a057

文献信息

• A convenient synthesis of 2′-deoxy-6-thioguanosine,<i>ara</i>-guanine,<i>ara</i>-6-thioguanine and certain related purine nucleosides by the stereospecific sodium salt glycosylation procedure
  作者：Naeem B. Hanna、Kandasamy Ramasamy、Roland K. Robins、Ganapathi R. Revankar

  DOI：10.1002/jhet.5570250653

  日期：1988.11

  A simple and high-yield synthesis of biologically significant 2′-deoxy-6-thioguanosine (11), ara-6-thioguanine (16) and araG (17) has been accomplished employing the Stereospecific sodium salt glycosylation method. Glycosylation of the sodium salt of 6-chloro- and 2-amino-6-chloropurine (1 and 2, respectively) with 1-chloro-2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranose (3) gave the corresponding

  使用立体特异性钠盐糖基化方法已经完成了生物学上重要的2'-脱氧-6-硫鸟嘌呤（11），ara -6-硫鸟嘌呤（16）和ara G（17）的简单且高收率的合成。6-氯-和2-氨基-6-氯嘌呤（分别为1和2）的钠盐与1-氯-2-脱氧-3,5-二-O-（对甲苯甲酰基）-α-的糖基化D-赤型-五呋喃糖（3）给出了相应的N-9取代核苷，它们是具有β-端基异构体构型的主要产物（4和5，以及少量的N-7位置异构体（6和7）。在含有甲醇钠的甲醇中用硫化氢处理4，以93％的收率得到2'-deoxy-6-thioinosine（10）。类似地，将5以71％的产率转化为2'-脱氧-6-硫鸟苷（β-TGdR，11）。2的钠盐与1-氯-2,3,5-三-O-苄基-α-D-阿拉伯呋喃糖（8）的反应分别得到N-7和N-9糖基化产物13和9。9的脱苄基作用用三氯化硼在-78°下用62％的收率得到通用的中间体2-氨基-6-氯
• Synthesis of 2'-deoxytubercidin, 2'-deoxyadenosine, and related 2'-deoxynucleosides via a novel direct stereospecific sodium salt glycosylation procedure
  作者：Zygmunt Kazimierczuk、Howard B. Cottam、Ganapathi R. Revankar、Roland K. Robins

  DOI：10.1021/ja00333a046

  日期：1984.10
• Method for the production of 2'-deoxyadenosine compounds
  申请人：BRIGHAM YOUNG UNIVERSITY

  公开号：EP0173059B1

  公开（公告）日：1989-11-29
• HANNA, NACEM B.;RAMASAMY, KANDASAMY;ROBINS, ROLAND K.;REVANKAR, GANAPATHI+, J. HETEROCYCL. CHEM., 25,(1988) N, C. 1899-1903
  作者：HANNA, NACEM B.、RAMASAMY, KANDASAMY、ROBINS, ROLAND K.、REVANKAR, GANAPATHI+

  DOI：——

  日期：——
• ROBINS, ROLAND K.;REVANKAR, GANAPATHI R.
  作者：ROBINS, ROLAND K.、REVANKAR, GANAPATHI R.

  DOI：——

  日期：——