3-O-p-tolylsulfonyl-2,5-anhydro-L-idofuranose dimethylacetal | 196596-83-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-p-tolylsulfonyl-2,5-anhydro-L-idofuranose dimethylacetal
• 英文别名: [(2R,3S,4R,5S)-2-(dimethoxymethyl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] 4-methylbenzenesulfonate
• CAS: 196596-83-5
• 化学式: C₁₅H₂₂O₈S
• 分子量: 362.401
• InChiKey: BBOHBJADFOVZNL-RFQIPJPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  甲醇 、 1,2-O-isopropylidene-3,5-di-O-p-tolylsulfonyl-6-O-benzoyl-α-D-glucofuranose 在 盐酸 作用下， 反应 70.0h， 以94.4%的产率得到3-O-p-tolylsulfonyl-2,5-anhydro-L-idofuranose dimethylacetal
  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.