5-乙酸乙酰氨基-4,7,8-三-O-乙酰基-9-叠氮-3,5,9-三脱氧-2-S-苯基-2-硫-D-丙三氧基-β-D-半乳-2-吡喃壬酮糖甲酯 | 1195053-25-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-乙酸乙酰氨基-4,7,8-三-O-乙酰基-9-叠氮-3,5,9-三脱氧-2-S-苯基-2-硫-D-丙三氧基-β-D-半乳-2-吡喃壬酮糖甲酯
• 英文名称: methyl (phenyl 5-acetoxyacetamido-4,7,8-tri-O-acetyl-9-azido-3,5,9-trideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate
• 英文别名: Methyl (Phenyl 5-Acetoxyacetamido-4,7,8-tri-O-acetyl-9-azido-3,5,9-trideoxy-2-thio-D-glycero-beta-D-galacto-2-nonulopyranosid)onate；methyl (2R,4S,5R,6R)-4-acetyloxy-5-[(2-acetyloxyacetyl)amino]-6-[(1R,2R)-1,2-diacetyloxy-3-azidopropyl]-2-phenylsulfanyloxane-2-carboxylate
• CAS: 1195053-25-8
• 化学式: C₂₆H₃₂N₄O₁₂S
• 分子量: 624.626
• InChiKey: YBDMZZOROXIIKI-YJGXBXLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  43
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  210
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  联苯-4-甲醇 、 5-乙酸乙酰氨基-4,7,8-三-O-乙酰基-9-叠氮-3,5,9-三脱氧-2-S-苯基-2-硫-D-丙三氧基-β-D-半乳-2-吡喃壬酮糖甲酯 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 乙腈 为溶剂， 以66%的产率得到methyl (4'-biphenylmethyl 5-acetoxyacetamido-4,7,8-tri-O-acetyl-9-azido-3,5,9-trideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  Potent small molecule mouse CD22-inhibitors: Exploring the interaction of the residue at C-2 of sialic acid scaffold

  摘要：

  Our previous study revealed that compound 1 (9-(4'-hydroxy-4-biphenyl)acetamido-9-deoxy-Neu5Gc alpha 2-6GalOMP) has the most promising affinity for mCD22. Replacing the subterminal galactose residue of 1 with benzyl or biphenylmethyl as aglycone led to 38- and 20-fold higher potency, respectively. This discovery represents a new direction in inhibitor design suitable for pharmaceutical development. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.044
• 作为产物：
  描述：

  、 乙酸酐 以 吡啶 为溶剂， 以1.08 g的产率得到5-乙酸乙酰氨基-4,7,8-三-O-乙酰基-9-叠氮-3,5,9-三脱氧-2-S-苯基-2-硫-D-丙三氧基-β-D-半乳-2-吡喃壬酮糖甲酯
  参考文献：
  名称：

  Potent small molecule mouse CD22-inhibitors: Exploring the interaction of the residue at C-2 of sialic acid scaffold

  摘要：

  Our previous study revealed that compound 1 (9-(4'-hydroxy-4-biphenyl)acetamido-9-deoxy-Neu5Gc alpha 2-6GalOMP) has the most promising affinity for mCD22. Replacing the subterminal galactose residue of 1 with benzyl or biphenylmethyl as aglycone led to 38- and 20-fold higher potency, respectively. This discovery represents a new direction in inhibitor design suitable for pharmaceutical development. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.044