1-[2,5-dideoxy-5-(methylamino)-β-D-threo-pentofuranosyl]thymine | 108169-95-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 2 '，5'-二脱氧核苷
• 英文名称: 1-[2,5-dideoxy-5-(methylamino)-β-D-threo-pentofuranosyl]thymine
• 英文别名: 1-[(2R,4R,5R)-4-hydroxy-5-(methylaminomethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 108169-95-5
• 化学式: C₁₁H₁₇N₃O₄
• 分子量: 255.274
• InChiKey: SMLUVDLCTDSENP-IWSPIJDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.29
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  96.35
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-[2,5-dideoxy-5-(methylamino)-β-D-threo-pentofuranosyl]thymine 在 叠氮化锂 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.75h， 生成 N-[(2R,3S,5R)-3-Azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-N-methyl-methanesulfonamide
  参考文献：
  名称：

  Synthesis of New 5″-Sulfonylamido Derivatives of 3″-Azido-3″-Deoxythymidine (AZT)

  摘要：

  A series of 5'-N-methanesulfonyl derivatives of 3'-azido-5'-(alkylamino)-3',5'-dideoxythymidine was synthesised. The first step of the synthesis involved the reaction of 1-(2,5-dideoxy-5-O-tosyl-beta-D-threo-pentofuranosyl)thymine 1 with an appropriate amine to give 1-[5-(alkylamino)-2,5-dideoxy-beta-D-threo-pentofuranosyl]thymine 2a-e and 1-(2,5-dideoxy-beta-threo-pent-4-enofuranosyl)thymine 3 as a by-product. Compounds 2a-e were treated with an excess of methanesulfonyl chloride to yield intermediates 1-[5-(dimethylamino)-3-O-methanesulfonyl-2,3,5-trideoxy-beta-D-threo-pentofuranosyl]thymine 4a and 1-[5-(N-alkyl-N-methanesulfonyl)-3-O-methanesulfonyl-2,3,5-trideoxy-beta-D-threo-penfuranosyl]thymines 4b-e. The reaction of 4a-e with lithium azide in dimethylformamide afforded the final compounds 1-[3-azido-5-(N-methyl-N-methanesulfonyl)-2,3,5-trideoxy-beta-D-erythro-penofuranosyl]thymine 5a and 1-[3-azido-5-(N-alkyl-N-methanesulfonyl)-2,3,5-trideoxy-beta-D-erythro-penofuranosyl]thymines 5b-e. The independent synthesis of 4',5'-unsaturated product 3 was also described.

  DOI：

  10.1080/07328319608007387
• 作为产物：
  描述：

  2,5'-(methylimino)-1-(2-deoxy-β-D-threo-pentafuranosyl)thymine 在 sodium hydroxide 作用下， 反应 20.0h， 以23%的产率得到1-[2,5-dideoxy-5-(methylamino)-β-D-threo-pentofuranosyl]thymine
  参考文献：
  名称：

  A novel two-step conversion of 3',5'-di-O-tosylthymidine to 5'-amino-5'-deoxythymidine analogs with inversion of the 3-hydroxyl group

  摘要：

  DOI：

  10.1021/jo00389a043

文献信息

• Photochemical removal of the tosyl group from the 5?N position of 5?-aminopyrimidine nucleosides: syntheticapplications
  作者：Wojciech Urjasz、Lech Celewicz

  DOI：10.1002/(sici)1099-1395(199808/09)11:8/9<618::aid-poc52>3.0.co;2-f

  日期：1998.8