methyl 2-(2'-oxoethyl)-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulosonate | 119054-25-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-(2'-oxoethyl)-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulosonate
• 英文别名: methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-(2-oxoethoxy)-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 119054-25-0
• 化学式: C₂₂H₃₁NO₁₄
• 分子量: 533.486
• InChiKey: LZPNZLDNQKAHFO-ZJGVECAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.28
• 重原子数：
  37.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 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-(2'-oxoethyl)-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulosonate 在 palladium on activated charcoal 氢气 、 sodium methylate 、 caesium carbonate 作用下， 以 甲醇 、 叔丁醇 为溶剂， 反应 14.0h， 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
• 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， 生成 methyl 2-(2'-oxoethyl)-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：

  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

• 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).