methyl 5-acetamido-2-(2-oxoethyl)-4,7-di-O-acetyl-3,5-dideoxy-β-L-arabino-2-heptulopyranosonate | 167157-10-0

• 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-(2-oxoethyl)-4,7-di-O-acetyl-3,5-dideoxy-β-L-arabino-2-heptulopyranosonate
• CAS: 167157-10-0
• 化学式: C₁₆H₂₃NO₁₀
• 分子量: 389.359
• InChiKey: SQYCNUCFDFUGOF-TTZDDIAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.14
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  143.53
• 氢给体数：
  1.0
• 氢受体数：
  10.0

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 、 methyl 5-acetamido-2-(2-oxoethyl)-4,7-di-O-acetyl-3,5-dideoxy-β-L-arabino-2-heptulopyranosonate 在 caesium carbonate 作用下， 以 叔丁醇 为溶剂， 反应 2.5h， 以100 mg的产率得到methyl 5-acetamido-2-<5''-(methyl 2',3'-dibenzoyl-6'-deoxy-β-L-galactopyranoside 4'-yl)-4''-oxopent-2''-en-1''-yl>-4,7-di-O-acetyl-3,5-dideoxy-β-L-arabino-2-heptulopyranosonate
  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 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 Amberlite IRA 400 、 二甲基硫 、 4 A molecular sieve 、 sodium methylate 、 silver salicylate 、 臭氧 作用下， 以 甲醇 为溶剂， 反应 11.5h， 生成 methyl 5-acetamido-2-(2-oxoethyl)-4,7-di-O-acetyl-3,5-dideoxy-β-L-arabino-2-heptulopyranosonate
  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