methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2<*>6)-2,3,4-tri-O-acetyl-6-thio-α-D-glucopyranoside | 104556-74-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2<*>6)-2,3,4-tri-O-acetyl-6-thio-α-D-glucopyranoside
• 英文别名: methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[[(2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-methoxyoxan-2-yl]methylsulfanyl]-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 104556-74-3
• 化学式: C₃₃H₄₇NO₂₀S
• 分子量: 809.797
• InChiKey: IDAJIUJIVTYPIM-RXXDZZTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  55
• 可旋转键数：
  24
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  293
• 氢给体数：
  1
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2<*>6)-2,3,4-tri-O-acetyl-6-thio-α-D-glucopyranoside 在 sodium hydroxide 、 sodium methylate 作用下， 生成 sodium;N-[(2R,3R,4S,6S)-6-carboxy-4-hydroxy-6-[[(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methylsulfanyl]-2-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-3-yl]ethanimidate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of N-Acetylneuraminic Acid-Based Rotavirus Inhibitors

  摘要：

  Rotavirus can cause several gastrointestinal disease, especially in infants and young children, and is particularly prevalent in Third-World countries. Therefore, the development of potential inhibitors of this virus is of great interest. The present study describes the synthesis and in vitro biological evaluation of a number of N-acethyneuraminic acid-based compounds as potential rotavirus inhibitors. Our data suggests that it is indeed possible to inhibit adhesion of the virus, and hence in vitro replication, with carbohydrate-based molecules, although this inhibition, dues appear to be strain dependent.

  DOI：

  10.1021/jm950611f
• 作为产物：
  描述：

  2-Thiosialic acid methyl ester peracetate 、 methyl 2,3,4-tri-O-acetyl-6-bromo-6-deoxy-α-D-glucopyranoside 在 二乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以82%的产率得到methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2<*>6)-2,3,4-tri-O-acetyl-6-thio-α-D-glucopyranoside
  参考文献：
  名称：

  一种制备N-乙酰神经氨酸硫糖苷的简单方法。

  摘要：

  DOI：

  10.1016/0008-6215(94)84064-4