6-deoxy-1,2:3,4-di-O-isopropylidene-6-(3-methylcarbodiimido)-α-D-galactopyranose

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 6-deoxy-1,2:3,4-di-O-isopropylidene-6-(3-methylcarbodiimido)-α-D-galactopyranose
• 化学式: C₁₄H₂₂N₂O₅
• 分子量: 298.339
• InChiKey: ATMDRSHMBOEATE-YBXAARCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  70.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-deoxy-1,2:3,4-di-O-isopropylidene-6-(3-methylcarbodiimido)-α-D-galactopyranose 在 硫化氢 、 silica gel 作用下， 以 甲苯 为溶剂， 以90%的产率得到6-deoxy-1,2:3,4-di-O-isopropylidene-6-(N'-methylthioureido)-α-D-galactopyranose
  参考文献：
  名称：

  Synthesis of glycosyl(thio)ureido sugars via carbodiimides and their conformational behaviour in water

  摘要：

  The preparation of sugar ureas and thioureas by nucleophilic addition of water or hydrogen sulfide, respectively, to sugar-derived carbodiimides has been examined. Acetic acid efficiently catalysed the formation of ureas, whereas silica gel was found to be a more convenient catalyst in the case of the thioxo analogues. The procedures have been exploited in the development of an amine- and isocyanate-free synthesis of urea- and thiourea-tethered pseudooligosaccharides via the corresponding glycosylcarbodiimido sugars. The fully unprotected compounds adopted, preferentially, the (Z,Z) configuration at the pseudoamide bonds in water solution.

  DOI：

  10.1016/s0008-6215(00)00040-9
• 作为产物：
  描述：

  6-azido-6-deoxy-1,2:3,4-di-O-isopropylidene-D-galactopyranose 、 异硫氰酸甲酯 在 三苯基膦 作用下， 以 甲苯 为溶剂， 以72%的产率得到6-deoxy-1,2:3,4-di-O-isopropylidene-6-(3-methylcarbodiimido)-α-D-galactopyranose
  参考文献：
  名称：

  通过aza-Wittig反应合成（1→6）-碳二亚胺系的假寡糖

  摘要：

  摘要报道了通过糖衍生的亚氨基正膦与异硫氰酸酯的氮杂-维蒂格偶合合成不对称糖碳二亚胺的方法。在6-叠氮基-6-脱氧糖和糖基异硫氰酸酯的磷酰内酯衍生物的情况下，该反应特别快速和有效，并且已在结合碳二亚胺桥的（1→6）连接的假二糖和三糖的一锅法制备中得到了利用。作为相应的脲基，硫脲基和胍基衍生物的方便前体。动力学方面的考虑表明，在三苯基膦和糖叠氮化物的施陶丁格反应的早期形成的糖磷叠氮化物是反应性中间体。

  DOI：

  10.1016/s0008-6215(97)10012-x

文献信息

• Aza-Wittig reaction of sugar isothiocyanates and sugar iminophosphoranes: An easy entry to unsymmetrical sugar carbodiimides
  作者：JoséM. García Fernández、Carmen Ortiz Mellet、Víctor M. Díaz Pérez、J. Fuentes、József Kovács、István Pintér

  DOI：10.1016/s0040-4039(97)00810-1

  日期：1997.6

  towards the aza-Wittig condensation with isothiocyanates as compared with glycosyl phosphinimines. The reaction is particularly fast and efficient in the case of glycosyl isothiocyanates and has been exploited in the preparation of (1→6)-linked pseudooligosaccharides incorporating carbodiimide bridges. These compounds are excellent starting materials for the preparation of sugar ureas, thioureas and guanidines

  与伯氨酰基膦亚胺相比，在伯（C-6）位具有三苯基磷酰亚烷基氨基取代基的醛己糖衍生物显示出对与异硫氰酸酯的氮杂-维蒂希缩合反应的增加的反应性。在异硫氰酸糖基酯的情况下，该反应特别快速且有效，并且已被用于制备结合有碳二亚胺桥的（1→6）-连接的假低聚糖。这些化合物是通过与适当的亲核试剂反应制备糖脲，硫脲和胍的极好的起始原料。
• Synthesis of (1 → 6)-carbodiimide-tethered pseudooligosaccharides via aza-Wittig reaction
  作者：JoséManuel García Fernández、Carmen Ortiz Mellet、Víctor Manuel Díaz Pérez、José Fuentes、József Kovács、István Pintér

  DOI：10.1016/s0008-6215(97)10012-x

  日期：1997.11

  unsymmetrical sugar carbodiimides through aza-Wittig coupling of sugar derived iminophosphoranes and isothiocyanates is reported. The reaction is particularly fast and efficient in the case of phosphoranylide derivatives of 6-azido-6-deoxysugars and glycosyl isothiocyanates, and has been exploited in the one-pot preparation of (1 → 6)-linked pseudodi- and trisaccharides incorporating carbodiimide bridges as

  摘要报道了通过糖衍生的亚氨基正膦与异硫氰酸酯的氮杂-维蒂格偶合合成不对称糖碳二亚胺的方法。在6-叠氮基-6-脱氧糖和糖基异硫氰酸酯的磷酰内酯衍生物的情况下，该反应特别快速和有效，并且已在结合碳二亚胺桥的（1→6）连接的假二糖和三糖的一锅法制备中得到了利用。作为相应的脲基，硫脲基和胍基衍生物的方便前体。动力学方面的考虑表明，在三苯基膦和糖叠氮化物的施陶丁格反应的早期形成的糖磷叠氮化物是反应性中间体。
• Synthesis of glycosyl(thio)ureido sugars via carbodiimides and their conformational behaviour in water
  作者：Victor Manuel Dı́az Pérez、Carmen Ortiz Mellet*、José Fuentes、José Manuel Garcı́a Fernández*

  DOI：10.1016/s0008-6215(00)00040-9

  日期：2000.6

  The preparation of sugar ureas and thioureas by nucleophilic addition of water or hydrogen sulfide, respectively, to sugar-derived carbodiimides has been examined. Acetic acid efficiently catalysed the formation of ureas, whereas silica gel was found to be a more convenient catalyst in the case of the thioxo analogues. The procedures have been exploited in the development of an amine- and isocyanate-free synthesis of urea- and thiourea-tethered pseudooligosaccharides via the corresponding glycosylcarbodiimido sugars. The fully unprotected compounds adopted, preferentially, the (Z,Z) configuration at the pseudoamide bonds in water solution.