2,3'-anhydro-5'-deoxy-5'-N-morpholinothymidine

• 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: 2,3'-anhydro-5'-deoxy-5'-N-morpholinothymidine
• 英文别名: (1R,9R,10R)-4-methyl-10-(morpholin-4-ylmethyl)-8,11-dioxa-2,6-diazatricyclo[7.2.1.02,7]dodeca-3,6-dien-5-one
• 化学式: C₁₄H₁₉N₃O₄
• 分子量: 293.323
• InChiKey: JBEYFSZYMMHBFN-IJLUTSLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3'-anhydro-5'-deoxy-5'-N-morpholinothymidine 在 叠氮化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以62%的产率得到3',5'-dideoxy-3'-azido-5'-N-morpholinothymidine
  参考文献：
  名称：

  Reactions of dimesylthymidine with secondary amines: Easy access to 3′,5′-dideoxy-3′-substituted-5′-alkylaminothymidines - New classes of potential antiviral aminonucleosides.

  摘要：

  3,5'-Di-O-mesylthymidine 4a (DMST) on reaction with secondary amines undergoes hitherto unknown ''one-pot-two-steps'' transformation to produce 2,3'-O-anhydro-5'-deoxy-5'-alkylaminothymidines 5a-h. Most of the amines used, irrespective of their basicities showed remarkable selectivity towards the 5'-substitution over the 2,3'-O-anhydro ring formation. Compounds 5a-h could be used as intermediates for the synthesis of a variety of 3,5'-dideoxy-3'-substituted-5'-alkylaminothymidines of the type 9, 10a-b, 11.

  DOI：

  10.1016/s0040-4020(01)85753-7
• 作为产物：
  描述：

  5-O-(4-甲基苯基磺酰基)胸腺嘧啶脱氧核苷 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 102.0h， 生成 2,3'-anhydro-5'-deoxy-5'-N-morpholinothymidine
  参考文献：
  名称：

  Reactions of dimesylthymidine with secondary amines: Easy access to 3′,5′-dideoxy-3′-substituted-5′-alkylaminothymidines - New classes of potential antiviral aminonucleosides.

  摘要：

  3,5'-Di-O-mesylthymidine 4a (DMST) on reaction with secondary amines undergoes hitherto unknown ''one-pot-two-steps'' transformation to produce 2,3'-O-anhydro-5'-deoxy-5'-alkylaminothymidines 5a-h. Most of the amines used, irrespective of their basicities showed remarkable selectivity towards the 5'-substitution over the 2,3'-O-anhydro ring formation. Compounds 5a-h could be used as intermediates for the synthesis of a variety of 3,5'-dideoxy-3'-substituted-5'-alkylaminothymidines of the type 9, 10a-b, 11.

  DOI：

  10.1016/s0040-4020(01)85753-7

文献信息

• Reactions of dimesylthymidine with secondary amines: Easy access to 3′,5′-dideoxy-3′-substituted-5′-alkylaminothymidines - New classes of potential antiviral aminonucleosides.
  作者：K. Sakthivel、R.Krishna Kumar、T. Pathak

  DOI：10.1016/s0040-4020(01)85753-7

  日期：1993.1

  3,5'-Di-O-mesylthymidine 4a (DMST) on reaction with secondary amines undergoes hitherto unknown ''one-pot-two-steps'' transformation to produce 2,3'-O-anhydro-5'-deoxy-5'-alkylaminothymidines 5a-h. Most of the amines used, irrespective of their basicities showed remarkable selectivity towards the 5'-substitution over the 2,3'-O-anhydro ring formation. Compounds 5a-h could be used as intermediates for the synthesis of a variety of 3,5'-dideoxy-3'-substituted-5'-alkylaminothymidines of the type 9, 10a-b, 11.