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 | 152646-61-2

• 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 6'-deoxy-β-L-galactopyranoside-4'-yl)-4''-oxo-pent-2''-en-1''-yl>-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulosonate
• 英文别名: methyl (2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-[4-oxo-5-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methoxy-2-methyloxan-3-yl]pentoxy]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• CAS: 152646-61-2
• 化学式: C₂₄H₄₁NO₁₅
• 分子量: 583.587
• InChiKey: RMIDMWUCIDCJOJ-ZNOJXVMZSA-N

物化性质

• 沸点：
  892.6±65.0 °C(predicted)
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  251
• 氢给体数：
  8
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  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 在 sodium hydroxide 作用下， 以 水 为溶剂， 以100%的产率得到sodium 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：

  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
• 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 、 sodium methylate 、 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 28.0h， 生成 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：

  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

文献信息

• A novel mimic of the sialyl Lewis x determinant
  作者：Nigel M. Allanson、Alan H. Davidson、Fionna M. Martin

  DOI：10.1016/s0040-4039(00)79271-9

  日期：1993.6

  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.
• The synthesis of novel mimics of the sialyl Lewis X determinant
  作者：Nigel M. Allanson、Alan H. Davidson、Christopher D. Floyd、Fionna M. Martin

  DOI：10.1016/s0957-4166(00)86284-9

  日期：1994.11

  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).