3-benzylthiopropyl 5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosonic acid methyl ester | 325962-14-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzylthiopropyl 5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosonic acid methyl ester
• CAS: 325962-14-9
• 化学式: C₂₂H₃₃NO₉S
• 分子量: 487.571
• InChiKey: ZVZPMBLUBFSGFC-ZJGVECAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.44
• 重原子数：
  33.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  154.78
• 氢给体数：
  5.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3-benzylthiopropyl 5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosonic acid methyl ester 在 sodium hydroxide 作用下， 反应 1.0h， 以100%的产率得到3-benzylthiopropyl 5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosonic 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：

  allyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,54-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosonic acid methyl ester 在 偶氮二异丁腈 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 3-benzylthiopropyl 5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosonic acid methyl ester
  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