2,3-O-Isopropylidene-5-O-(1-methoxyethyl)-6-O-(p-tolylsulfonyl)-D-mannofuranose

• 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: 2,3-O-Isopropylidene-5-O-(1-methoxyethyl)-6-O-(p-tolylsulfonyl)-D-mannofuranose
• 英文别名: [(2R)-2-[(3aS,6R,6aS)-4-hydroxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-2-(1-methoxyethoxy)ethyl] 4-methylbenzenesulfonate
• 化学式: C₁₉H₂₈O₉S
• 分子量: 432.492
• InChiKey: JJSRIPTXXRAIJJ-BCYWLMFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3-O-Isopropylidene-5-O-(1-methoxyethyl)-6-O-(p-tolylsulfonyl)-D-mannofuranose 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以25%的产率得到1,6':6,1'-dianhydro-2,3:2',3'-di-O-isopropylidene-5,5'-di-O-(1-methoxyethyl)-di-α-D-mannofuranose
  参考文献：
  名称：

  2,3,4-Tri-O-acetyl-1,6-anhydro-β-d-mannopyranose, an artifact produced during carbohydrate analysis. A total synthesis of 2,3,5-tri-O-acetyl-1,6-anhydro-β-d-mannofuranose

  摘要：

  This study confirms that 2,3,4-tri-O-acetyl-1,6-anhydro-beta-D-mannopyranose is an artifact produced during carbohydrate analysis. A new synthesis of 2,3,5-tri-O-acetyl-1,6-anhydro-beta-D-mannofuranose is also described, and a novel dimer, 1,6':6,1'-dianhydro-2,3:2',3'-di-O-isopropylidene-5,5'-di-O-(1-methoxyethyl)-di-alpha-D-mannofuranose, has been isolated. The structure of the dimer is confirmed by X-ray analysis of a derivative, 1,6':6,1'-dianhydro-2,3:2',3'-di-O-isopropylidene-di-alpha-D-mannofuranose.

  DOI：

  10.1016/0008-6215(93)84078-k
• 作为产物：
  描述：

  2,3:5,6-二-O-异亚丙基-D-甘露糖酸-1,4-内酯 在 吡啶 、 水 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 溶剂黄146 作用下， 以 正己烷 、 氯仿 、 甲苯 为溶剂， 反应 69.0h， 生成 2,3-O-Isopropylidene-5-O-(1-methoxyethyl)-6-O-(p-tolylsulfonyl)-D-mannofuranose
  参考文献：
  名称：

  2,3,4-Tri-O-acetyl-1,6-anhydro-β-d-mannopyranose, an artifact produced during carbohydrate analysis. A total synthesis of 2,3,5-tri-O-acetyl-1,6-anhydro-β-d-mannofuranose

  摘要：

  This study confirms that 2,3,4-tri-O-acetyl-1,6-anhydro-beta-D-mannopyranose is an artifact produced during carbohydrate analysis. A new synthesis of 2,3,5-tri-O-acetyl-1,6-anhydro-beta-D-mannofuranose is also described, and a novel dimer, 1,6':6,1'-dianhydro-2,3:2',3'-di-O-isopropylidene-5,5'-di-O-(1-methoxyethyl)-di-alpha-D-mannofuranose, has been isolated. The structure of the dimer is confirmed by X-ray analysis of a derivative, 1,6':6,1'-dianhydro-2,3:2',3'-di-O-isopropylidene-di-alpha-D-mannofuranose.

  DOI：

  10.1016/0008-6215(93)84078-k

文献信息

• 2,3,4-Tri-O-acetyl-1,6-anhydro-β-d-mannopyranose, an artifact produced during carbohydrate analysis. A total synthesis of 2,3,5-tri-O-acetyl-1,6-anhydro-β-d-mannofuranose
  作者：Sukumar Manna、Bill H. McAnalley、Herman L. Ammon

  DOI：10.1016/0008-6215(93)84078-k

  日期：1993.4

  This study confirms that 2,3,4-tri-O-acetyl-1,6-anhydro-beta-D-mannopyranose is an artifact produced during carbohydrate analysis. A new synthesis of 2,3,5-tri-O-acetyl-1,6-anhydro-beta-D-mannofuranose is also described, and a novel dimer, 1,6':6,1'-dianhydro-2,3:2',3'-di-O-isopropylidene-5,5'-di-O-(1-methoxyethyl)-di-alpha-D-mannofuranose, has been isolated. The structure of the dimer is confirmed by X-ray analysis of a derivative, 1,6':6,1'-dianhydro-2,3:2',3'-di-O-isopropylidene-di-alpha-D-mannofuranose.