4-N-acetamidophenyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid) onate | 144988-66-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-N-acetamidophenyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid) onate
• 英文别名: methyl (2S,4S,5R,6R)-5-acetamido-2-(4-acetamidophenyl)sulfanyl-4-acetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 144988-66-9
• 化学式: C₂₈H₃₆N₂O₁₃S
• 分子量: 640.665
• InChiKey: PPWCDHUQJRTYEM-LJXJJVDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  224
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1,2-di-O-tetradecyl-sn-glycerol 、 4-N-acetamidophenyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid) onate 在 氰化汞 、 DMTST 、 mercury dibromide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.5h， 以81%的产率得到(4S,5R,6R)-4-Acetoxy-5-acetylamino-2-((R)-2,3-bis-tetradecyloxy-propoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  “Active” and “latent” thioglycosyl donors in oligosaccharide synthesis. Application to the synthesis of α-sialosides

  摘要：

  The use of a new "active" and "latent" thioglycosyl donor strategy in glycoside synthesis is described using arylthio alpha-sialosides of different reactivities.

  DOI：

  10.1016/s0040-4039(00)60004-7
• 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 、 乙醇 、 四丁基硫酸氢铵 、 sodium carbonate 、 tin(ll) chloride 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 生成 4-N-acetamidophenyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid) onate
  参考文献：
  名称：

  Mild stereoselective syntheses of thioglycosides under PTC conditions and their use as active and latent glycosyl donors

  摘要：

  Mild and stereoselective arylthio glycoside syntheses were accomplished by inversion of configuration of glycosyl halides under phase transfer catalyzed conditions. Under such conditions, aryl alpha-thiosialosides having electron donating and withdrawing substituents were evaluated as active and latent thioglycosyl donors. A sialyl-alpha-(2-->6)-galactoside was prepared in good yield using the above strategy.

  DOI：

  10.1016/s0957-4166(00)86308-9