1-(2'-O,3'-O-Cyclopentyl-5'-O-benzyl-β-D-erythro-pentofuranosyl)-N¹-benzylinosine | 161824-94-8

• 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: 1-(2'-O,3'-O-Cyclopentyl-5'-O-benzyl-β-D-erythro-pentofuranosyl)-N¹-benzylinosine
• 英文别名: 9-[(3aR,4R,6R,6aR)-6-(phenylmethoxymethyl)spiro[3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-2,1'-cyclopentane]-4-yl]-1-benzylpurin-6-one
• CAS: 161824-94-8
• 化学式: C₂₉H₃₀N₄O₅
• 分子量: 514.581
• InChiKey: CRMNWJVBWSEEMJ-ZYWWQZICSA-N

物化性质

• 沸点：
  760.4±70.0 °C(predicted)
• 密度：
  1.43±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  87.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2'-O,3'-O-Cyclopentyl-5'-O-benzyl-β-D-erythro-pentofuranosyl)-N¹-benzylinosine 在 吡啶 、 三氟乙酸 作用下， 反应 17.0h， 生成 Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(1-benzyl-6-oxo-1,6-dihydro-purin-9-yl)-5-benzyloxymethyl-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  A Facile Route to Pyrimidine-Based Nucleoside Olefins: Application to the Synthesis of d4T (Stavudine)

  摘要：

  An efficient synthetic route to nucleoside olefins in the uridine, cytidine, and thymidine series is described which utilizes the Garegg-Samuelsson iodine/triphenylphosphine/imidazole-promoted deoxygenation of the 2',3'-hydroxyl groups as the key step. Cyclopentylidene ketal protection was employed for all the nucleoside 2',3'-hydroxyls to facilitate blocking of the 5'-hydroxyl and the pyrimidine nitrogens with the benzyl or 4-methoxybenzyl (PMB) groups. Deblocking of the cyclopentylidene group followed by olefination of the resulting diols provided protected nucleoside olefins 18-20. Starting with 5-methyluridine 4 and utilizing the 4-methoxybenzyl group for 5',N-3 protection, the overall scheme provided the anti-HIV compound d4T (1) after deprotection of the PMB groups. The dibenzylhypoxanthine nucleoside diol 17 derived from inosine gave either unreacted starting material or decomposition products under several sets of conditions.

  DOI：

  10.1021/jo00103a017
• 作为产物：
  描述：

  1,1-二甲氧基环戊烷 在 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 1-(2'-O,3'-O-Cyclopentyl-5'-O-benzyl-β-D-erythro-pentofuranosyl)-N¹-benzylinosine
  参考文献：
  名称：

  A Facile Route to Pyrimidine-Based Nucleoside Olefins: Application to the Synthesis of d4T (Stavudine)

  摘要：

  An efficient synthetic route to nucleoside olefins in the uridine, cytidine, and thymidine series is described which utilizes the Garegg-Samuelsson iodine/triphenylphosphine/imidazole-promoted deoxygenation of the 2',3'-hydroxyl groups as the key step. Cyclopentylidene ketal protection was employed for all the nucleoside 2',3'-hydroxyls to facilitate blocking of the 5'-hydroxyl and the pyrimidine nitrogens with the benzyl or 4-methoxybenzyl (PMB) groups. Deblocking of the cyclopentylidene group followed by olefination of the resulting diols provided protected nucleoside olefins 18-20. Starting with 5-methyluridine 4 and utilizing the 4-methoxybenzyl group for 5',N-3 protection, the overall scheme provided the anti-HIV compound d4T (1) after deprotection of the PMB groups. The dibenzylhypoxanthine nucleoside diol 17 derived from inosine gave either unreacted starting material or decomposition products under several sets of conditions.

  DOI：

  10.1021/jo00103a017

文献信息

• Synthesis of 2′,3′-Dideoxyinosine via Radical Deoxygenation
  作者：Takayoshi Torii、Kunisuke Izawa、Dae Hyan Cho、Doo Ok Jang

  DOI：10.1080/15257770701508414

  日期：2007.11.26

  A synthetic method for 2 ′,3 ′-dideoxyinosine (ddI) from inosine was established via radical deoxygenation of N1,5 ′-O-diprotected-2 ′,3 ′-bis-S-methyl dithiocarbonate of inosine derivatives. The radical deoxygenation proceeded smoothly to give the desired dideoxy compounds in good yields using 1-ethylpiperidinium hypophosphite and triethylborane. Benzyl or p-methoxybenzyl protection of inosine at

  通过肌苷衍生物的N1,5'-O-diprotected-2',3'-双-S-甲基二硫代碳酸酯的自由基脱氧，建立了由肌苷合成2',3'-二脱氧肌苷(ddI)的方法。使用 1-乙基哌啶鎓次磷酸盐和三乙基硼烷，自由基脱氧顺利进行，以良好的收率得到所需的双脱氧化合物。N1、5'-O-位肌苷的苄基或对甲氧基苄基保护对ddI合成有效。
• A Facile Route to Pyrimidine-Based Nucleoside Olefins: Application to the Synthesis of d4T (Stavudine)
  作者：Frederick A. Luzzio、Michael E. Menes

  DOI：10.1021/jo00103a017

  日期：1994.12

  An efficient synthetic route to nucleoside olefins in the uridine, cytidine, and thymidine series is described which utilizes the Garegg-Samuelsson iodine/triphenylphosphine/imidazole-promoted deoxygenation of the 2',3'-hydroxyl groups as the key step. Cyclopentylidene ketal protection was employed for all the nucleoside 2',3'-hydroxyls to facilitate blocking of the 5'-hydroxyl and the pyrimidine nitrogens with the benzyl or 4-methoxybenzyl (PMB) groups. Deblocking of the cyclopentylidene group followed by olefination of the resulting diols provided protected nucleoside olefins 18-20. Starting with 5-methyluridine 4 and utilizing the 4-methoxybenzyl group for 5',N-3 protection, the overall scheme provided the anti-HIV compound d4T (1) after deprotection of the PMB groups. The dibenzylhypoxanthine nucleoside diol 17 derived from inosine gave either unreacted starting material or decomposition products under several sets of conditions.