N-[(2R,3R)-4-Acetylamino-3-hydroxy-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyl]-acetamide | 181045-87-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2R,3R)-4-Acetylamino-3-hydroxy-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyl]-acetamide
• CAS: 181045-87-4
• 化学式: C₃₅H₄₄N₂O₈
• 分子量: 620.743
• InChiKey: SZLVOQCVMVGJMO-RHDSNWPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  45.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  124.58
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-[(2R,3R)-4-Acetylamino-3-hydroxy-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyl]-acetamide 在 palladium on activated charcoal N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 氢气 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 1.0h， 生成 {(2R,3R,4S,5S,6R)-2-[(1R,2R)-3-Acetylamino-1-(acetylamino-methyl)-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-propoxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-acetic acid
  参考文献：
  名称：

  Mimics of the sialyl Lewis X tetrasaccharide. Replacement of the N-Acetylglucosamine sugar with simple C2-symmetric 1,2-diols

  摘要：

  Analogues of sialyl Lewis X have been synthesized that feature replacement of the N-acetylglucosamine residue with C-2-symmetric diols. The diols used contain different levels of torsional constraint and various functional groups. The cyclohexyl derived compound 27 was equipotent to sLex in vitro (IC50 0.5 mM). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00055-7
• 作为产物：
  描述：

  N-[5R-(acetylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4R-ylmethyl]-acetamide 在 4 A molecular sieve 、 四乙基溴化铵 、 溴 、 三氟乙酸 作用下， 反应 3.08h， 生成 N-[(2R,3R)-4-Acetylamino-3-hydroxy-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyl]-acetamide
  参考文献：
  名称：

  Mimics of the sialyl Lewis X tetrasaccharide. Replacement of the N-Acetylglucosamine sugar with simple C2-symmetric 1,2-diols

  摘要：

  Analogues of sialyl Lewis X have been synthesized that feature replacement of the N-acetylglucosamine residue with C-2-symmetric diols. The diols used contain different levels of torsional constraint and various functional groups. The cyclohexyl derived compound 27 was equipotent to sLex in vitro (IC50 0.5 mM). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00055-7