3,4-di-O-benzoyl-1,5-anhydro-L-rhamnulose | 1170109-46-2

• 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: 3,4-di-O-benzoyl-1,5-anhydro-L-rhamnulose
• 英文别名: [(2S,3S,4R)-4-benzoyloxy-2-methyl-5-oxooxan-3-yl] benzoate
• CAS: 1170109-46-2
• 化学式: C₂₀H₁₈O₆
• 分子量: 354.359
• InChiKey: WKTVEDKFLDYZLL-KKXDTOCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4-di-O-benzoyl-1,5-anhydro-L-rhamnulose 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 0.08h， 以87%的产率得到(6S)-4-benzoyloxy-6-methyl-2H-pyran-3(6H)-one
  参考文献：
  名称：

  A convenient access to the 1,5-anhydro forms of d-tagatose, l-rhamnulose and d-xylulose via 2-hydroxyglycal esters

  摘要：

  Zemplen methanolysis or a three-step protocol comprising hydroxylaminolysis, de-O-acetylation and deoximination smoothly and efficiently convert the benzoylated 2-hydroxy-D-glycals Of D-galactose, L-rhamnose and D-Xylose into their configurationally related 1,5-anhydro-ketoses, thereby providing convenient access to the 1,5-anhydro forms of D-tagatose, L-rhamnulose and D-Xylulose. Invariably obtained as amorphous solids, they are best characterized through their highly crystalline oximes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.016
• 作为产物：
  描述：

  3,4-di-O-benzoyl-6-deoxy-α-L-arabino-hexopyranos-2-ulosyl bromide 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以71%的产率得到3,4-di-O-benzoyl-1,5-anhydro-L-rhamnulose
  参考文献：
  名称：

  A convenient access to the 1,5-anhydro forms of d-tagatose, l-rhamnulose and d-xylulose via 2-hydroxyglycal esters

  摘要：

  Zemplen methanolysis or a three-step protocol comprising hydroxylaminolysis, de-O-acetylation and deoximination smoothly and efficiently convert the benzoylated 2-hydroxy-D-glycals Of D-galactose, L-rhamnose and D-Xylose into their configurationally related 1,5-anhydro-ketoses, thereby providing convenient access to the 1,5-anhydro forms of D-tagatose, L-rhamnulose and D-Xylulose. Invariably obtained as amorphous solids, they are best characterized through their highly crystalline oximes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.016

文献信息

• A convenient access to the 1,5-anhydro forms of d-tagatose, l-rhamnulose and d-xylulose via 2-hydroxyglycal esters
  作者：Pan Jarglis、Volker Göckel、Frieder W. Lichtenthaler

  DOI：10.1016/j.tetasy.2009.03.016

  日期：2009.5

  Zemplen methanolysis or a three-step protocol comprising hydroxylaminolysis, de-O-acetylation and deoximination smoothly and efficiently convert the benzoylated 2-hydroxy-D-glycals Of D-galactose, L-rhamnose and D-Xylose into their configurationally related 1,5-anhydro-ketoses, thereby providing convenient access to the 1,5-anhydro forms of D-tagatose, L-rhamnulose and D-Xylulose. Invariably obtained as amorphous solids, they are best characterized through their highly crystalline oximes. (C) 2009 Elsevier Ltd. All rights reserved.