methyl 2,3-di-O-benzoyl-4-(3'-dimethylphosphono-2'-oxo-propan-1-yl)-6-deoxy-β-L-galactopyranoside | 152646-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzoyl-4-(3'-dimethylphosphono-2'-oxo-propan-1-yl)-6-deoxy-β-L-galactopyranoside
• CAS: 152646-57-6
• 化学式: C₂₆H₃₁O₁₁P
• 分子量: 550.499
• InChiKey: SAQUCSRDTGDWRT-MSJBHRNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  143.89
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzoyl-4-(3'-dimethylphosphono-2'-oxo-propan-1-yl)-6-deoxy-β-L-galactopyranoside 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 caesium carbonate 作用下， 以 甲醇 、 叔丁醇 为溶剂， 25.0~30.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 生成 methyl 5-acetamido-2-<5''-(methyl 2',3'-di-O-benzoyl-6'-deoxy-β-L-galactopyranoside-4'-yl)-4''-hydroxy-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：

  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 三异丙氧基氯化钛 、 正丁基锂 、 4 A molecular sieve 、 sodium hydride 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 methyl 2,3-di-O-benzoyl-4-(3'-dimethylphosphono-2'-oxo-propan-1-yl)-6-deoxy-β-L-galactopyranoside
  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

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.