1-(6-amino-2-chloro-purin-9-yl)-O³,O⁵-bis-(4-methyl-benzoyl)-α-D-erythro-1,2-dideoxy-pentofuranose | 39031-33-9

• 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: 1-(6-amino-2-chloro-purin-9-yl)-O³,O⁵-bis-(4-methyl-benzoyl)-α-D-erythro-1,2-dideoxy-pentofuranose
• 英文别名: 2-chloro-6-amino-9-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythropentofuranosyl) purine；[(2R,3S,5S)-5-(6-amino-2-chloropurin-9-yl)-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 39031-33-9
• 化学式: C₂₆H₂₄ClN₅O₅
• 分子量: 521.96
• InChiKey: KQIOLKMXWDMQGA-ZCNNSNEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  37
• 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：
  131
• 氢给体数：
  1
• 氢受体数：
  9

文献信息

• Method for the production of 2-chloro-2' -deoxyadenosine (cladribine) and its 3,5-di-O-p-toluoyl derivative
  申请人：——

  公开号：US20020052491A1

  公开（公告）日：2002-05-02

  A process for the production of cladribine, 2-chloro-2′-deoxyadenosine, is provided which involves the direct glycosylation of 2-chloro-6-aminopurine with 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-&agr;-D-erythropentofuranose. The process is carried out by first forming the sodium salt of 2-chloro-6-aminopurine and allowing the sodium salt to react with 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-&agr;-D-erythropentofuranose in the presence of a moderately polar solvent such as acetone. The final product, cladribine, is produced by removal of the p-toluoyl groups by the action of methanolic ammonia or methanolic sodium methoxide.

  提供一种制备克拉德利宾（2-氯-2'-脱氧腺苷）的方法，其中涉及将2-氯-6-氨基嘌呤直接与1-氯-2-脱氧-3,5-二-O-p-甲苯基-&agr;-D-红细胞五糖苷化。该过程首先通过形成2-氯-6-氨基嘌呤的钠盐，并在存在适度极性溶剂（如丙酮）的情况下使钠盐与1-氯-2-脱氧-3,5-二-O-p-甲苯基-&agr;-D-红细胞五糖反应。最终产品克拉德利宾是通过使用甲醇氨或甲醇甲基钠的作用去除p-甲苯基基团而产生的。
• [EN] METHOD FOR THE PRODUCTION OF 2-CHLORO-2'-DEOXYADENOSINE (CLADRIBINE) AND ITS 3,5-DI-O-p-TOLUOYL DERIVATIVE<br/>[FR] PROCEDE DE PRODUCTION DE 2-CHLORO-2'-DESOXYADENOSINE (CLADRIBINE) ET SON DERIVE 3,5-DI-O-P-TOLUOYLE
  申请人：STERRENBELD BIOTECHNOLOGIE NORTH AMERICA INC

  公开号：WO2000064918A1

  公开（公告）日：2000-11-02

  A process for the production of cladribine, 2-chloro-2'-deoxyadenosine, is provided which involves the direct glycosylation of 2-chloro-6-aminopurine with 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-erythropentofuranose. The process is carried out by first forming the sodium salt of 2-chloro-6-aminopurine and allowing the sodium salt to react with 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-erythropentofuranose in the presence of a moderately polar solvent such as acetone. The final product, cladribine, is produced by removal of the p-toluoyl groups by the action of methanolic ammonia or methanolic sodium methoxide.

  提供一种生产克拉德利宾（2-氯-2'-脱氧腺苷）的方法，其中包括将2-氯-6-氨基嘌呤直接与1-氯-2-脱氧-3,5-二-O-对甲苯磺酰-α-D-赤藓糖苷化。该过程首先通过形成2-氯-6-氨基嘌呤的钠盐，并在中等极性溶剂（如丙酮）的存在下使钠盐与1-氯-2-脱氧-3,5-二-O-对甲苯磺酰-α-D-赤藓糖反应。最终产物克拉德利宾是通过甲醇氨或甲醇甲氧基钠的作用去除对甲苯磺酰基而得到的。