methyl 2-deoxy-2-fluoro-D-ribofuranoside | 149714-04-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-deoxy-2-fluoro-D-ribofuranoside
• 英文别名: methyl 2-deoxy-2-fluoro-beta-D-ribofuranoside；(2R,3R,4R,5R)-4-fluoro-2-(hydroxymethyl)-5-methoxyoxolan-3-ol
• CAS: 149714-04-5
• 化学式: C₆H₁₁FO₄
• 分子量: 166.149
• InChiKey: ULRUFWVRASYVEG-KVTDHHQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-deoxy-2-fluoro-D-ribofuranoside 在 三氟乙酸 作用下， 反应 42.0h， 生成 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-D-ribofuranose
  参考文献：
  名称：

  Synthesis and Biologic Activity of Purine 2′-Deoxy-2′-fluoro-ribonucleosides

  摘要：

  The synthesis of 3,5-di-O-benzoyl-2-deoxy-2-fluoro-D-ribofuranosyl bromide (8) and its reaction with 2,6-dichloropurine by fusion and with mercuric cyanide catalysis is described. The resulting 2,6-dichloro-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-beta-D-ribofuranosyl)purine (13) was converted to the 2-fluoroadenine (16), the 2-chloroadenine (17), 2,6-diaminopurine (12), and guanine (14) nucleosides by standard procedures. These nucleosides were cytotoxic to a number of cell lines in culture. The 2-haloadenine nucleosides 16 and 17 gave modest increases in lifespan when tested against the P388 leukemia in mice.

  DOI：

  10.1080/15257779408013243
• 作为产物：
  描述：

  methyl 3,5-di-O-(4-chlorobenzyl)-D-arabinofuranoside 在 palladium on activated charcoal 吡啶 、 四丁基氟化铵 、 氢气 、 magnesium oxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 methyl 2-deoxy-2-fluoro-D-ribofuranoside
  参考文献：
  名称：

  Synthesis and Biologic Activity of Purine 2′-Deoxy-2′-fluoro-ribonucleosides

  摘要：

  The synthesis of 3,5-di-O-benzoyl-2-deoxy-2-fluoro-D-ribofuranosyl bromide (8) and its reaction with 2,6-dichloropurine by fusion and with mercuric cyanide catalysis is described. The resulting 2,6-dichloro-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-beta-D-ribofuranosyl)purine (13) was converted to the 2-fluoroadenine (16), the 2-chloroadenine (17), 2,6-diaminopurine (12), and guanine (14) nucleosides by standard procedures. These nucleosides were cytotoxic to a number of cell lines in culture. The 2-haloadenine nucleosides 16 and 17 gave modest increases in lifespan when tested against the P388 leukemia in mice.

  DOI：

  10.1080/15257779408013243

文献信息

• Processes for preparing 2'-deoxy-2'-fluorocoformycin and stereoisomers
  申请人：Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai

  公开号：US05773607A1

  公开（公告）日：1998-06-30

  2'-Deoxy-2'-fluorocoformycin and 2'-deoxy-8-epi-2'-fluorocoformycin are synthesized in this invention through a multi-stage process via 3,5-di-O-benzoyl-2-deoxy-2-fluoro-.alpha.- and -.beta.-D-ribofuranosyl bromides. Further, according to this invention, 2'-deoxy-2'-epi-2'-fluorocoformycin and 2'-deoxy-8,2'-diepi-2'-fluorocoformycin are synthesized by a multi-stage process starting from 3,5-di-O-benzoyl-2-deoxy-2-fluoro-.alpha.-D-arabinofuranosyl bromide. These four 2'-fluoro derivatives of coformycin are novel compounds and have high enzyme-inhibitory activities against adenosine deaminase. In particular, these novel compounds are useful substances which exhibit therapeutic effects on acute lymphocytic leukemias due to their high enzyme-inhibitory activities above-mentioned. In addition, a variety of intermediates are obtained as novel compounds which are useful for the synthesis of the aforesaid novel 2'-fluoro derivatives of coformycin.

  本发明通过经过多阶段的过程，通过3,5-二-O-苯甲酰基-2-脱氧-2-氟-.alpha.-和-.beta.-D-核糖溴化物合成了2'-脱氧-2'-氟可酶霉素和2'-脱氧-8-表-2'-氟可酶霉素。此外，根据本发明，从3,5-二-O-苯甲酰基-2-脱氧-2-氟-.alpha.-D-阿拉伯核糖溴化物开始，通过多阶段过程合成了2'-脱氧-2'-表-2'-氟可酶霉素和2'-脱氧-8,2'-双表-2'-氟可酶霉素。这四种2'-氟可酶霉素衍生物是新化合物，并且对腺苷脱氨酶具有高的酶抑制活性。特别是，这些新化合物是有用的物质，因为它们具有上述高酶抑制活性，对急性淋巴细胞白血病具有治疗作用。此外，还获得了多种中间体作为新化合物，这些中间体对于合成上述新的2'-氟可酶霉素衍生物是有用的。
• 2'-deoxy-2'-epi-2'-fluorocoformycin
  申请人：Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai

  公开号：US05886167A1

  公开（公告）日：1999-03-23

  2'-Deoxy-2'-fluorocoformycin and 2'-deoxy-8-epi-2'-fluorocoformycin are synthesized in this invention through a multi-stage process via 3,5-di-O-benzoyl-2-deoxy-2-fluoro-.alpha.- and -.beta.-D-ribofuranosyl bromides. Further, according to this invention, 2'-deoxy-2'-epi-2'-fluorocoformycin and 2'-deoxy-8,2'-diepi-2'-fluorocoformycin are synthesized by a multi-stage process starting from 3,5-di-O-benzoyl-2-deoxy-2-fluoro-.alpha.-D-arabinofuranosyl bromide. These four 2'-fluoro derivatives of coformycin are novel compounds and have high enzyme-inhibitory activities against adenosine deaminase. In particular, these novel compounds are useful substances which exhibit therapeutic effects on acute lymphocytic leukemias due to their high enzyme-inhibitory activities above-mentioned. In addition, a variety of intermediates are obtained as novel compounds which are useful for the synthesis of the aforesaid novel 2'-fluoro derivatives of coformycin.

  本发明通过经过多阶段的过程，通过3,5-二-O-苯甲酰基-2-脱氧-2-氟-α-和β-D-核糖溴化物合成了2'-脱氧-2'-氟可酶霉素和2'-脱氧-8-表-2'-氟可酶霉素。此外，根据本发明，通过从3,5-二-O-苯甲酰基-2-脱氧-2-氟-α-D-阿拉伯核糖溴化物开始的多阶段过程，合成了2'-脱氧-2'-表-2'-氟可酶霉素和2'-脱氧-8,2'-二表-2'-氟可酶霉素。这四种2'-氟可酶霉素衍生物是新化合物，并且对腺苷脱氨酶具有高酶抑制活性。特别是，由于其上述高酶抑制活性，这些新化合物是具有治疗急性淋巴细胞白血病的有用物质。此外，还获得了多种中间体作为新化合物，这些中间体对合成上述新的2'-氟可酶霉素衍生物是有用的。
• 2'-DEOXY-2'-FLUOROCOFORMYCIN AND STEREOISOMERS THEREOF
  申请人：ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI

  公开号：EP0643069A1

  公开（公告）日：1995-03-15

  2'-Deoxy-2'-fluorocoformycin and 2'-deoxy-8-epi-2'-fluorocoformycin have now been synthesized by a multistage reaction via 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α- and -β-D-ribofuranosyl bromide. Also 2'-deoxy-2'-epi-2'-fluorocoformycin and 2'-deoxy-8,2'-diepi-2'-fluorocoformycin have been synthesized from 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranosyl bromide by a multistage reaction. These four 2'-fluorocoformycin derivatives are novel compounds and have a potent enzyme inhibiting activity against adenosine deaminase. In particular, they are useful for treating acute lymphocytic leukemia in virtue of the above activity. Other novel compounds also obtained include various intermediates useful for the synthesis of the above derivatives.

  2'-Deoxy-2'-fluorocoformycin 和 2'-deoxy-8-epi-2'-fluorocoformycin 现已通过 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α- 和 -β-D-ribofuranosyl bromide 的多级反应合成。此外，3,5-二-O-苯甲酰基-2-脱氧-2-氟-α-D-阿拉伯呋喃糖基溴化物通过多级反应合成了 2'-deoxy-2'-epi-2'-fluorocoformycin 和 2'-deoxy-8,2'-diepi-2'-fluorocoformycin 。这四种 2'-氟甲酰霉素衍生物是新型化合物，对腺苷脱氨酶具有强效的酶抑制活性。由于具有上述活性，它们特别适用于治疗急性淋巴细胞白血病。此外，还获得了其他新型化合物，包括用于合成上述衍生物的各种中间体。
• US5773607A
  申请人：——

  公开号：US5773607A

  公开（公告）日：1998-06-30
• US5886167A
  申请人：——

  公开号：US5886167A

  公开（公告）日：1999-03-23