2,5-脱水-4-脱氧-4-(3,4-二氢-2,4-二氧代-1(2H)-嘧啶基)-1-(二甲基缩醛)-L-甘露糖 | 196596-84-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,5-脱水-4-脱氧-4-(3,4-二氢-2,4-二氧代-1(2H)-嘧啶基)-1-(二甲基缩醛)-L-甘露糖
• 英文名称: 4-deoxy-4-(uracil-1-yl)-2,5-anhydro-L-mannofuranose dimethylacetal
• 英文别名: 1-[(2R,3R,4R,5R)-5-(dimethoxymethyl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]pyrimidine-2,4-dione
• CAS: 196596-84-6
• 化学式: C₁₂H₁₈N₂O₇
• 分子量: 302.284
• InChiKey: RTOYHFGCVJLIAL-BEYHFKMWSA-N

物化性质

• 密度：
  1.414±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,5-脱水-4-脱氧-4-(3,4-二氢-2,4-二氧代-1(2H)-嘧啶基)-1-(二甲基缩醛)-L-甘露糖 在 sodium azide 、 四溴化碳 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 为溶剂， 反应 17.0h， 以92%的产率得到6'-deoxy-6'-azido-4'-deoxy-4'-(uracil-1-yl)-2',5'-anhydro-L-mannofuranose dimethyl acetal
  参考文献：
  名称：

  One-step synthesis of novel tricyclic isomeric azidonucleosides

  摘要：

  Several tricyclic azido-isonucleosides were formed in high yields by the treatment of pyrimidine isonucleosides with triphenylphosphine, tetrabromomethane, and sodium azide. The regioselective ring opening of these tricyclic azido-isonucleosides was also investigated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.03.034
• 作为产物：
  描述：

  3-O-p-tolylsulfonyl-2,5-anhydro-L-idofuranose dimethylacetal 在 甲醇 、 18-冠醚-6 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 2,5-脱水-4-脱氧-4-(3,4-二氢-2,4-二氧代-1(2H)-嘧啶基)-1-(二甲基缩醛)-L-甘露糖
  参考文献：
  名称：

  Stereoselective synthesis of 4-deoxy-4-nucleobase-2,5-anhydro-l-mannitol derivatives

  摘要：

  2,5:3,4-Dianhydro-L-talofuranose dimethylacetal 7 was synthesized from D-glucose in 7 steps. A series of 4-deoxy-4-nucleobase-2,5-anhydro-L-mannitols 13-16 were synthesized regioselectively from 7 in good yields. 6-O-p-Tolylsulfonyl-2,5:3,4-dianhydro-L-talofuranose dimethylacetal 8 reacted with uracil or thymine to give the corresponding isonucleosides 17 and 19, but in the case of reaction of 8 with adenine, reformation of tetrahydrofuran ring took place, giving 4-(S)-adenyl-5-(R)-[1'-(R)-hydroxy-2',2'-dimethoxyl] ethyl-2,3-dihydrofuran 21 and 4-deoxy-4-adenyl-2,5:3,6-dianhydro-L-mannofuranose dimethylacetal 22. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00314-5

文献信息

• Stereoselective synthesis of 4-deoxy-4-nucleobase-2,5-anhydro-l-mannitol derivatives
  作者：Z.J. Yang、H.W. Yu、J.M. Min、L.T. Ma、L.H. Zhang

  DOI：10.1016/s0957-4166(97)00314-5

  日期：1997.8

  2,5:3,4-Dianhydro-L-talofuranose dimethylacetal 7 was synthesized from D-glucose in 7 steps. A series of 4-deoxy-4-nucleobase-2,5-anhydro-L-mannitols 13-16 were synthesized regioselectively from 7 in good yields. 6-O-p-Tolylsulfonyl-2,5:3,4-dianhydro-L-talofuranose dimethylacetal 8 reacted with uracil or thymine to give the corresponding isonucleosides 17 and 19, but in the case of reaction of 8 with adenine, reformation of tetrahydrofuran ring took place, giving 4-(S)-adenyl-5-(R)-[1'-(R)-hydroxy-2',2'-dimethoxyl] ethyl-2,3-dihydrofuran 21 and 4-deoxy-4-adenyl-2,5:3,6-dianhydro-L-mannofuranose dimethylacetal 22. (C) 1997 Elsevier Science Ltd.
• One-step synthesis of novel tricyclic isomeric azidonucleosides
  作者：Zong-Sheng Li、Ren-Ping Qiao、Zhen-Jun Yang、Liang-Ren Zhang、Li-He Zhang

  DOI：10.1016/j.tetasy.2006.03.034

  日期：2006.4

  Several tricyclic azido-isonucleosides were formed in high yields by the treatment of pyrimidine isonucleosides with triphenylphosphine, tetrabromomethane, and sodium azide. The regioselective ring opening of these tricyclic azido-isonucleosides was also investigated. (c) 2006 Elsevier Ltd. All rights reserved.