6-chloro-9-(3-O-benzoyl-β-D-ribofuranosyl)purine | 228243-48-9

• 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: 6-chloro-9-(3-O-benzoyl-β-D-ribofuranosyl)purine
• 英文别名: 6-chloropurin-9-yl 3'-O-benzoylriboside；6-chloropurine 3'-O-benzoylriboside；3'-O-benzoyl-6-chloropurine riboside；[(2R,3S,4R,5R)-5-(6-chloropurin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] benzoate
• CAS: 228243-48-9
• 化学式: C₁₇H₁₅ClN₄O₅
• 分子量: 390.783
• InChiKey: PSTWMLRHPHPNRY-XNIJJKJLSA-N

物化性质

• 沸点：
  662.9±65.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-chloro-9-(3-O-benzoyl-β-D-ribofuranosyl)purine 在 palladium on activated charcoal diamide 、 氨 、 氢气 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 为溶剂， 生成 腺苷
  参考文献：
  名称：

  A New Method for the Synthesis of 2′-O-Benzyladenosine Using Mitsunobu Reaction

  摘要：

  A new method to introduce a benzyl group onto the 2'-OH of purine ribonucleoside is described. Thus, 6-chloropurine 3'-O-benzoylriboside and its 5'-O-trityl congener were condensed with benzyl alcohol using the Mitsunobu reaction to give the 2'-O-benzyl derivative. The yields were varied from 4.6 to 62.9% depending on the solvent used. The product was converted to adenosine, indicating that the stereochemistry at C-2' is retained.

  DOI：

  10.1081/ncn-120019506
• 作为产物：
  描述：

  6-氯嘌呤核苷 、 苯甲酰氯 在 二正丁基氧化锡 、 三乙胺 作用下， 以 甲醇 为溶剂， 以65%的产率得到6-chloro-9-(3-O-benzoyl-β-D-ribofuranosyl)purine
  参考文献：
  名称：

  An Industrial Process for Synthesizing Lodenosine (FddA)

  摘要：

  Two industrial synthetic approaches to Lodenosine (1, FddA, 9-(2,3-dideoxy-2-fluoro-p-D-threo-pentofuranosyl) adenine) via a purine riboside or a purine 3'-deoxyriboside are described. Several novel applications of deoxygenation and fluorination methods are compared considering reaction yields, economy, safety and environmental concerns.

  DOI：

  10.1081/ncn-120021951

文献信息

• Synthesis of 9-(2-Deoxy-2-fluoro-.BETA.-D-arabinofuranosyl)adenine Bearing a Selectively Removable Protecting Group.
  作者：Tokumi MARUYAMA、Satoshi TAKAMATSU、Shigetada KOZAI、Yoshiko SATOH、Kunisuke IZAWA

  DOI：10.1248/cpb.47.966

  日期：——

  A facile and practicam method to infroduce fluorine at the up-side of the 2'-carbon of nucleosides is described. 6-Chloropurine riboside 3 was converted to the 3'-O-benzoate 4a via a stannylene complex, then converted to the 3'-O-benzoyl-5'-O-tritylriboside 5a. In the presence of pyridine, migration of the 3'-benzoyl groups of 4a and 5a to 2'-OH was rather slow. Hence, 5a was reacted with diethylaminosulfur trifluoride (DAST) in CH2Cl2 in the presence of pyridine to give the 2'-deoxy-2'-fluoroarabinoside 6 in good yield. The 3'-O-benzoyl-5'-O-trityl protecting system was easy to deprotect selectively. Thus, treatment of 6 with ammonia in MeOH gave the 5'-O-trityl compound 7, which was subjected to esterificaiton with phenyl chlorothionoformate, radical deoxygenation with tris(trimethylsilyl)silane and acid treatment to afford 9-(2, 3-dideoxy-2-fluoro-β-D-threo-pento-furanosyl)adenine(FddA) 2. In addition, acid treatment of 7 gave 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine (FdaraA) 1.

  本文介绍了一种在核苷 2'- 碳的上侧生成氟的简便实用的方法。6- 氯嘌呤核苷 3 通过斯坦尼烯络合物转化为 3'-O- 苯甲酸 4a，然后转化为 3'-O- 苯甲酰基-5'-O-三苯甲基核苷 5a。在吡啶存在的情况下，4a 和 5a 的 3'- 苯甲酰基向 2'-OH 的迁移相当缓慢。因此，在吡啶存在下，5a 在 CH2Cl2 中与二乙基三氟化硫（DAST）反应，得到 2'-deoxy-2'-fluoroarabinoside 6，收率很高。3'-O- 苯甲酰基-5'-O-三苯甲基保护体系很容易选择性地脱保 护。因此，用 MeOH 中的氨水处理 6，可得到 5'-O- 三苯甲基化合物 7，该化合物经氯硫代甲酸苯酯化、三（三甲基硅基）硅烷自由基脱氧和酸处理后，可得到 9-(2,3-二脱氧-2-氟-β-D-三戊基-呋喃糖基)腺嘌呤（FddA）2。此外，酸处理 7 得到 9-(2-脱氧-2-氟-β-D-阿拉伯呋喃糖基)腺嘌呤（FdaraA）1。
• Introduction of a Benzyl Group onto the 2′-OH of 6-Chloropurine 3′-<i>O</i>-Benzoylriboside
  作者：Shigetada Kozai、Tomoyo Fuzikawa、Keisuke Harumoto、Tokumi Maruyama

  DOI：10.1081/ncn-120022633

  日期：2003.10

  A new method to introduce a benzyl group onto the 2'-OH of purine ribonucleoside is described. Thus, 6-chloropurine 3'-O-benzoylriboside and its 5'-O-trityl congener were condensed with benzyl alcohol using the Mitsunobu reaction to give the 2'-O-benzyl derivative. The yields were varied from 4.6 to 62.9%, depending on the solvent. The product was converted to adenosine, indicating that the stereochemistry at C-2' is retained.
• PROCESS FOR PRODUCING NUCLEOSIDE DERIVATIVES
  申请人：Ajinomoto Co., Inc.

  公开号：EP1052265B1

  公开（公告）日：2005-12-07
• Introduction of a benzoyl group onto riboside in aqueous solution: One-step synthesis of 6-chloropurine 2′,3′-di-O-benzoylriboside
  作者：Shigetada Kozai、Satoshi Takamatsu、Kunisuke Izawa、Tokumi Maruyama

  DOI：10.1016/s0040-4039(99)00747-9

  日期：1999.6

  A benzoyl group was introduced onto the 3'-hydroxyl group of 6-chloropurine riboside by treatment with benzoylating agents in the presence of an organic or inorganic base in aqueous solution, in which further reaction gave 6-chloropurine 2',3'-di-O-benzoylriboside. (C) 1999 Elsevier Science Ltd. Ali rights reserved.
• An Industrial Process for Synthesizing Lodenosine (FddA)
  作者：Kunisuke Izawa、Satoshi Takamatsu、Satoshi Katayama、Naoko Hirose、Shigetaka Kozai、Tokumi Maruyama

  DOI：10.1081/ncn-120021951

  日期：2003.10

  Two industrial synthetic approaches to Lodenosine (1, FddA, 9-(2,3-dideoxy-2-fluoro-p-D-threo-pentofuranosyl) adenine) via a purine riboside or a purine 3'-deoxyriboside are described. Several novel applications of deoxygenation and fluorination methods are compared considering reaction yields, economy, safety and environmental concerns.