(2S,3R)-2-acetamido-3-(((2S,3R,4R,5R,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-N-methylbutanamide | 947382-72-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R)-2-acetamido-3-(((2S,3R,4R,5R,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-N-methylbutanamide
• CAS: 947382-72-1
• 化学式: C₃₆H₄₅N₃O₈
• 分子量: 647.769
• InChiKey: PNKWHDYMHDBUHM-XVJDXOJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  47.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  133.45
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-acetamido-3-(((2S,3R,4R,5R,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-N-methylbutanamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以88%的产率得到(2S,3R)-2-acetamido-3-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-N-methylbutanamide
  参考文献：
  名称：

  Serine versus Threonine Glycosylation:  The Methyl Group Causes a Drastic Alteration on the Carbohydrate Orientation and on the Surrounding Water Shell

  摘要：

  Different behavior has been observed for the psi torsion angle of the glycosidic linkages of d-GalNAc-Ser and d-GalNAc-Thr motifs, allowing the carbohydrate moiety to adopt a completely different orientation. In addition, the fact that the water pockets found in alpha-d-GalNAc-Thr differ from those obtained for its serine analogue could be related to the different capability that the two model glycopeptides have to structure the surrounding water. This fact could have important biological inferences (i.e., antifreeze activity).

  DOI：

  10.1021/ja072181b
• 作为产物：
  描述：

  3,4,6-tri-O-benzyl-2-nitro-D-galactal 在 Ni Raney (T₄) 吡啶 、 potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 31.0h， 生成 (2S,3R)-2-acetamido-3-(((2S,3R,4R,5R,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-N-methylbutanamide
  参考文献：
  名称：

  Serine versus Threonine Glycosylation:  The Methyl Group Causes a Drastic Alteration on the Carbohydrate Orientation and on the Surrounding Water Shell

  摘要：

  Different behavior has been observed for the psi torsion angle of the glycosidic linkages of d-GalNAc-Ser and d-GalNAc-Thr motifs, allowing the carbohydrate moiety to adopt a completely different orientation. In addition, the fact that the water pockets found in alpha-d-GalNAc-Thr differ from those obtained for its serine analogue could be related to the different capability that the two model glycopeptides have to structure the surrounding water. This fact could have important biological inferences (i.e., antifreeze activity).

  DOI：

  10.1021/ja072181b