methyl (3-benzylthiopropyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate | 325962-08-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (3-benzylthiopropyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate
• CAS: 325962-08-1
• 化学式: C₂₃H₃₀O₁₀S
• 分子量: 498.551
• InChiKey: PBFITPVXRVOEGY-YKZCJQPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  34.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl (3-benzylthiopropyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以69%的产率得到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
• 作为产物：
  描述：

  allyl 2,3,4-tri-O-acetyl-6-O-trityl-β-D-glucopyranoside 在 chromium(VI) oxide 、 偶氮二异丁腈 、 硫酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.33h， 生成 methyl (3-benzylthiopropyl 2,3,4-tri-O-acetyl-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