6-O-p-tolylsulfonyl-2,5:3,4-dianhydro-L-talofuranose dimethylacetal | 67492-43-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-O-p-tolylsulfonyl-2,5:3,4-dianhydro-L-talofuranose dimethylacetal
• 英文别名: 2,5:3,4-Dianhydro-L-talose Dimethyl Acetal p-Toluenesulfonate；[(1R,2S,4R,5R)-4-(dimethoxymethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 67492-43-7
• 化学式: C₁₅H₂₀O₇S
• 分子量: 344.386
• InChiKey: IDFAUHPJGORGNU-REWJHTLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  92
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-O-p-tolylsulfonyl-2,5:3,4-dianhydro-L-talofuranose dimethylacetal 在 氨 作用下， 反应 72.0h， 以93%的产率得到1-Amino-4-(4-methyl-3-nitrophenoxy)butane
  参考文献：
  名称：

  New, easily removable poly(ethylene glycol) supports for the liquid-phase method of peptide synthesis

  摘要：

  DOI：

  10.1021/jo01314a032
• 作为产物：
  描述：

  1,2-O-Isopropyliden-3,5,6-tri-O-p-toluolsulfonyl-α-D-glucofuranose 在 盐酸 、 甲醇 、 potassium carbonate 作用下， 反应 146.5h， 生成 6-O-p-tolylsulfonyl-2,5:3,4-dianhydro-L-talofuranose 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

• Total synthesis and revised structural assignment of (+)-furanomycin
  作者：Madeleine M. Joullie、Pen C. Wang、J. Edward Semple

  DOI：10.1021/ja00522a095

  日期：1980.1
• Synthesis of (2R,4S,5S)-epiallomuscarine, (2S,3R,5S)-isoepiallomuscarine, and (2S,3S,4S,5S)-3-hydroxyepiallomuscarine from .alpha.-D-glucose
  作者：Pen-Chung Wang、Madeleine M. Joullie

  DOI：10.1021/jo01314a031

  日期：1980.12
• New, easily removable poly(ethylene glycol) supports for the liquid-phase method of peptide synthesis
  作者：V. N. Rajasekharan Pillai、Manfred Mutter、Ernst Bayer、Ian Gatfield

  DOI：10.1021/jo01314a032

  日期：1980.12
• 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.