((2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(methylsulfonyloxy)-tetrahydrofuran-2-yl)methyl acetate | 162650-52-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: ((2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(methylsulfonyloxy)-tetrahydrofuran-2-yl)methyl acetate
• 英文别名: 5'-O-acetyl-3'-O-methanesulfonylthymidine；[(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-3-methylsulfonyloxyoxolan-2-yl]methyl acetate
• CAS: 162650-52-4
• 化学式: C₁₃H₁₈N₂O₈S
• 分子量: 362.361
• InChiKey: YVCOIANJBRKQCP-HBNTYKKESA-N

物化性质

• 密度：
  1.48±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ((2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(methylsulfonyloxy)-tetrahydrofuran-2-yl)methyl acetate 以 乙醇 为溶剂， 生成 Zidovudine
  参考文献：
  名称：

  Pyrimidine nucleoside derivatives and methods for producing them

  摘要：

  核苷衍生物，如2'-脱氧-2'-溴-5'-O-乙酰-5-甲基尿苷等，是重要的中间体，可以转化为核苷衍生物，如3'-氮杂-3'-脱氧胸苷等，这些对药物具有用处。

  公开号：

  US05633366A1
• 作为产物：
  描述：

  5'-O-acetylthymidine 、 甲基磺酰氯 在 二氯甲烷 、 水 、 Sodium sulfate-III 作用下， 以 吡啶 为溶剂， 反应 3.0h， 以to obtain 10.4 g of 5'-O-acetyl-3'-O-methanesulfonylthymidine的产率得到((2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(methylsulfonyloxy)-tetrahydrofuran-2-yl)methyl acetate
  参考文献：
  名称：

  Pyrimidine nucleoside derivatives and methods for producing them

  摘要：

  核苷衍生物，例如2'-脱氧-2'-溴-5'-O-乙酰-5-甲基尿嘧啶等，是重要的中间体，可转化为3'-偶氮-3'-脱氧胸腺嘧啶等核苷衍生物，这些核苷衍生物可用作药物。

  公开号：

  US05633366A1

文献信息

• Nucleoside derivatives and methods for producing them
  申请人：Ajinomoto Co., Inc.

  公开号：EP0638586A2

  公开（公告）日：1995-02-15

  An industrially useful method for producing 3'-azido-3'-deoxythymidine and its related compounds is provided. Further provided are nucleoside derivatives such as 2'-deoxy-2'-bromo-5'-O-acetyl-5-methyluridine, etc., which are important intermediates to be converted into nucleoside derivatives, such as 3'-azido-3'-deoxythymidine, etc. valuable as medicines. Also provided are a method for producing them and a method for converting the compounds into nucleoside derivatives such as 3'-azido-3'-deoxythymidine, etc.

  本发明提供了一种生产 3'-叠氮-3'-脱氧胸苷及其相关化合物的工业实用方法。 此外，还提供了核苷衍生物，如 2'-deoxy-2'-bromo-5'-O-acetyl-5-methyluridine 等，它们是转化为核苷衍生物，如 3'-azido-3'-deoxythymidine 等有价值药物的重要中间体。此外，还提供了生产这些化合物的方法以及将这些化合物转化为核苷衍生物（如 3'-azido-3'-deoxythymidine 等）的方法。
• Inversion of secondary chiral alcohols in toluene with the tunable complex of R3NR′COOH
  作者：Xiao-Xin Shi、Chun-Li Shen、Jian-Zhong Yao、Liang-Deng Nie、Na Quan

  DOI：10.1016/j.tetasy.2009.12.028

  日期：2010.3

  The S(N)2 reaction of enantiomerically pure sulfonates with the tunable complex of R3N-R'COOH in toluene has been extensively studied. It was revealed that the molar ratio of the tertiary amines and carboxylic acids in the complex of R3NR'COOH is crucial for the S(N)2 reaction, and should be tuned for each sulfonate to give the best yield. Fifteen sulfonates 1 and 3-13 (Scheme 2) were prepared and transformed into 22 corresponding inverted esters 2 and 14-24 (Scheme 2) in good to high yields. (C) 2010 Elsevier Ltd. All rights reserved.
• US5633366A
  申请人：——

  公开号：US5633366A

  公开（公告）日：1997-05-27