3,6-di-O-p-tolylsulfonyl-2,5-anhydro-L-idofuranose dimethylacetal | 39022-34-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-di-O-p-tolylsulfonyl-2,5-anhydro-L-idofuranose dimethylacetal
• 英文别名: 2,5-Anhydro-3,6-di-O-tosyl-L-idose Dimethyl Acetal；[(2S,3R,4S,5R)-5-(dimethoxymethyl)-3-hydroxy-4-(4-methylphenyl)sulfonyloxyoxolan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 39022-34-9
• 化学式: C₂₂H₂₈O₁₀S₂
• 分子量: 516.59
• InChiKey: DJOQKXIJPWNMDF-JSXRDJHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  151
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,6-di-O-p-tolylsulfonyl-2,5-anhydro-L-idofuranose dimethylacetal 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 2,5-anhydro-3,4,6-tri-O-benzoyl-L-mannose dimethyl acetal
  参考文献：
  名称：

  Ricciardy, Fiore; Joullie, Madeleine M., Synthetic Communications, 1986, vol. 16, # 1, p. 35 - 42

  摘要：

  DOI：
• 作为产物：
  描述：

  甲醇 、 1,2-O-Isopropyliden-3,5,6-tri-O-p-toluolsulfonyl-α-D-glucofuranose 在 盐酸 作用下， 反应 144.0h， 以87.2%的产率得到3,6-di-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

• Total synthesis of (+)-furanomycin and stereoisomers
  作者：J. Edward Semple、Pen C. Wang、Zenon Lysenko、Madeleine M. Joullie

  DOI：10.1021/ja00545a018

  日期：1980.12
• 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
• Ricciardy, Fiore; Joullie, Madeleine M., Synthetic Communications, 1986, vol. 16, # 1, p. 35 - 42
  作者：Ricciardy, Fiore、Joullie, Madeleine M.

  DOI：——

  日期：——
• 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.