Methanesulfonic acid (2R,3R,5R)-2-[(methanesulfonyl-methyl-amino)-methyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester | 179043-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: Methanesulfonic acid (2R,3R,5R)-2-[(methanesulfonyl-methyl-amino)-methyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3R,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-[[methyl(methylsulfonyl)amino]methyl]oxolan-3-yl] methanesulfonate
• CAS: 179043-86-8
• 化学式: C₁₃H₂₁N₃O₈S₂
• 分子量: 411.457
• InChiKey: NMQGBXZYAXLERT-GMTAPVOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.63
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  144.84
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (2R,3R,5R)-2-[(methanesulfonyl-methyl-amino)-methyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 在 叠氮化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 以55%的产率得到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：

  1-(2,5-dideoxy-5-O-tosyl-β-D-threo-pentofuranosyl)thymine 以 吡啶 、 乙腈 为溶剂， 反应 24.0h， 生成 Methanesulfonic acid (2R,3R,5R)-2-[(methanesulfonyl-methyl-amino)-methyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
  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