methyl 2-(4'-oxobutan-1'-yl)-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulosonate | 142301-35-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-(4'-oxobutan-1'-yl)-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulosonate
• CAS: 142301-35-7
• 化学式: C₂₄H₃₅NO₁₄
• 分子量: 561.54
• InChiKey: VUMDWRGIKLJHKP-KZXFCMPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  39.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  196.13
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(4'-oxobutan-1'-yl)-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulosonate 在 sodium tetrahydroborate 、 cerium(III) chloride 、 sodium methylate 、 caesium carbonate 作用下， 以 甲醇 、 乙醇 、 叔丁醇 为溶剂， 反应 38.67h， 生成 methyl 5-acetamido-2-<7''-(methyl 6'-deoxy-β-L-galactopyranoside-4'-yl)-6''-hydroxy-hept-4''-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：

  N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 在 二甲基硫 、 4 A molecular sieve 、 silver salicylate 、 臭氧 作用下， 反应 10.0h， 生成 methyl 2-(4'-oxobutan-1'-yl)-5-acetamido-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