methyl (3-benzylthiopropyl β-D-glucopyranosid)uronate | 325962-09-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (3-benzylthiopropyl β-D-glucopyranosid)uronate
• CAS: 325962-09-2
• 化学式: C₁₇H₂₄O₇S
• 分子量: 372.439
• InChiKey: LCPPIEYGRHILCI-KSXIZUIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.31
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  105.45
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl (3-benzylthiopropyl β-D-glucopyranosid)uronate 在 sodium hydroxide 作用下， 反应 0.25h， 以94.7%的产率得到3-benzylpropyl β-D-glucopyranosyluronic acid
  参考文献：
  名称：

  Introduction of monosaccharides having functional groups onto a carbosilane dendrimer: A broadly applicable one-pot reaction in liquid ammonia involving Birch reduction and subsequent Sn2 reaction

  摘要：

  Benzylthioalkyl glycosides of D-glucuronic acid, N-acetyl-D-glucosamine, and N-acetylneuraminic acid (common monosaccharide constituents of natural oligosaccharide chains) have been prepared as sulfide precursors for the carbohydrate coating of dendric carbosilane cores and used in a generally applicable one-pot reaction (Birch reduction in liquid ammonia and subsequent SN2 reaction) to generate a thioether linkage between the monosaccharide moieties and a carbosilane dendrimer. The dendrimers were uniformly functionalized with the monosaccharides in good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00247-0
• 作为产物：
  描述：

  (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-allyloxy-tetrahydro-pyran-2-carboxylic acid 在 偶氮二异丁腈 、 sodium methylate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 methyl (3-benzylthiopropyl β-D-glucopyranosid)uronate
  参考文献：
  名称：

  Introduction of monosaccharides having functional groups onto a carbosilane dendrimer: A broadly applicable one-pot reaction in liquid ammonia involving Birch reduction and subsequent Sn2 reaction

  摘要：

  Benzylthioalkyl glycosides of D-glucuronic acid, N-acetyl-D-glucosamine, and N-acetylneuraminic acid (common monosaccharide constituents of natural oligosaccharide chains) have been prepared as sulfide precursors for the carbohydrate coating of dendric carbosilane cores and used in a generally applicable one-pot reaction (Birch reduction in liquid ammonia and subsequent SN2 reaction) to generate a thioether linkage between the monosaccharide moieties and a carbosilane dendrimer. The dendrimers were uniformly functionalized with the monosaccharides in good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00247-0