methyl 5-acetamido-2-<5''-(methyl 2',3'-di-O-benzoyl-6'-deoxy-β-L-galactopyranoside-4'-yl)-4''-oxo-pent-1''-yl>-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulosonate | 152957-11-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-acetamido-2-<5''-(methyl 2',3'-di-O-benzoyl-6'-deoxy-β-L-galactopyranoside-4'-yl)-4''-oxo-pent-1''-yl>-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulosonate
• CAS: 152957-11-4
• 化学式: C₄₆H₅₇NO₂₁
• 分子量: 959.953
• InChiKey: QNWKKWDCTFTOOU-WDSITIKMSA-N

物化性质

• 沸点：
  964.6±65.0 °C(predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  68.0
• 可旋转键数：
  21.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  287.42
• 氢给体数：
  2.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  methyl 5-acetamido-2-<5''-(methyl 2',3'-di-O-benzoyl-6'-deoxy-β-L-galactopyranoside-4'-yl)-4''-oxo-pent-1''-yl>-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulosonate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以66%的产率得到methyl 5-acetamido-2-<5''-(methyl 6'-deoxy-β-L-galactopyranoside-4'-yl)-4''-oxo-pent-2''-en-1''-yl>-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulosonate
  参考文献：
  名称：

  The synthesis of novel mimics of the sialyl Lewis X determinant

  摘要：

  Disaccharide mimics of the sialyl Lewis X (sLe(x)) ligands have been prepared as potential antagonists of binding to the lectin domains-of the E-selectin adhesion molecule. Versatile derivatives of sialic acid provide an entry to a series of simplified linker groups supporting the fucose and sialyl residues. The stereoselectivity of nucleophilic addition to the fucosyl ketone derivative 7 is determined by the conditions employed; basic and Lewis acid conditions give opposite results(1).

  DOI：

  10.1016/s0957-4166(00)86284-9
• 作为产物：
  描述：

  methyl 2,3-O-dibenzoyl-α-L-fucopyranoside 在 palladium on activated charcoal 三异丙氧基氯化钛 、 4 A molecular sieve 、 氢气 、 caesium carbonate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 16.0h， 生成 methyl 5-acetamido-2-<5''-(methyl 2',3'-di-O-benzoyl-6'-deoxy-β-L-galactopyranoside-4'-yl)-4''-oxo-pent-1''-yl>-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulosonate
  参考文献：
  名称：

  A novel mimic of the sialyl Lewis x determinant

  摘要：

  The syntheses of two novel disaccharides are described which block the interaction of the lectin domain of E-selectin with its glycosylated ligands on neutrophils.

  DOI：

  10.1016/s0040-4039(00)79271-9