7-(3-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)thio)propoxy)-2H-chromen-2-one | 1350638-47-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-(3-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)thio)propoxy)-2H-chromen-2-one
• CAS: 1350638-47-9
• 化学式: C₁₈H₂₂O₈S
• 分子量: 398.434
• InChiKey: AYGVCUAPCXMULN-XNJHUCFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.09
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  129.59
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  7-(3-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)thio)propoxy)-2H-chromen-2-one 在 吡啶 、 N-碘代丁二酰亚胺 、 β3-N-acetylglucosaminyltransferase 、 silver trifluoromethanesulfonate 、 manganese(ll) chloride 、 bovine serum albumin 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Rapid Chemo-Enzymatic Synthesis of Peracetylated GlcNAcβ3Galβ-Aglycones

  摘要：

  The inhibition of sialyl Lewis X can prevent unwanted cellular extravasation that is associated with inflammatory diseases and tumor metastasis. Described is an efficient methodology to prepare peracetylated GlcNAc beta 3Gal-aglycone disaccharides subsequently used as metabolic decoys to inhibit sialyl Lewis X expression. Four glycosides were synthesized from one single parent disaccharide that in turn was prepared by large-scale enzymatic synthesis. The procedure avoids lengthy and inefficient synthetic steps to afford the desired disaccharides quickly with good overall yields.

  DOI：

  10.1080/07328303.2011.617023
• 作为产物：
  描述：

  7-allyloxycoumarin 在 甲醇 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 7-(3-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)thio)propoxy)-2H-chromen-2-one
  参考文献：
  名称：

  Rapid Chemo-Enzymatic Synthesis of Peracetylated GlcNAcβ3Galβ-Aglycones

  摘要：

  The inhibition of sialyl Lewis X can prevent unwanted cellular extravasation that is associated with inflammatory diseases and tumor metastasis. Described is an efficient methodology to prepare peracetylated GlcNAc beta 3Gal-aglycone disaccharides subsequently used as metabolic decoys to inhibit sialyl Lewis X expression. Four glycosides were synthesized from one single parent disaccharide that in turn was prepared by large-scale enzymatic synthesis. The procedure avoids lengthy and inefficient synthetic steps to afford the desired disaccharides quickly with good overall yields.

  DOI：

  10.1080/07328303.2011.617023