N-acetyl-N-allyl-2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosylamine | 176664-28-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-acetyl-N-allyl-2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosylamine
• 英文别名: [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[acetyl(prop-2-enyl)amino]oxan-2-yl]methyl acetate
• CAS: 176664-28-1
• 化学式: C₁₉H₂₈N₂O₉
• 分子量: 428.439
• InChiKey: RYTDTBGEHPAJGH-FVVUREQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-acetyl-N-allyl-2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosylamine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 9.0h， 生成 N-acetyl-N-(3-thio-(2-aminoethyl))propyl-2-acetamido-2-deoxy-β-D-glucopyranosylamine
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Neoglycopeptides:  Application to an α-Gal-Terminated Neoglycopeptide

  摘要：

  A novel methodology; for the enzymatic preparation from suitably derivatized oligosaccharides of N-linked neoglycopeptides using the microbial glutaminyl-peptide gamma -glutamyl transferase, transglutaminase (TGase), is described, N-Allyl glycosides of various oligosaccharides were photochemically coupled with cysteamine to yield amino-terminated thioether spacers, which were accepted by transglutaminase to transamidate the side-chain gamma -carboxamide group in the dipeptide Z-Gln-Gly.

  DOI：

  10.1021/jo001439c
• 作为产物：
  描述：

  D-GlcNAc 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 96.0h， 生成 N-acetyl-N-allyl-2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosylamine
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Neoglycopeptides:  Application to an α-Gal-Terminated Neoglycopeptide

  摘要：

  A novel methodology; for the enzymatic preparation from suitably derivatized oligosaccharides of N-linked neoglycopeptides using the microbial glutaminyl-peptide gamma -glutamyl transferase, transglutaminase (TGase), is described, N-Allyl glycosides of various oligosaccharides were photochemically coupled with cysteamine to yield amino-terminated thioether spacers, which were accepted by transglutaminase to transamidate the side-chain gamma -carboxamide group in the dipeptide Z-Gln-Gly.

  DOI：

  10.1021/jo001439c

文献信息

• An Efficient Synthesis of <i>N</i>-Allylglycosylamides from Unprotected Carbohydrates
  作者：Wayne Spevak、Falguni Dasgupta、Christopher J. Hobbs、Jon O. Nagy

  DOI：10.1021/jo9522522

  日期：1996.1.1

  Synthetic, multivalent, carbohydrate assemblies are important tools in studying the avidity of many naturally occuring lectins for their ligands. This report details a simple, high-yielding three-step procedure to convert unprotected carbohydrates into N-allylglycosides. This method compliments the reductive amination procedure but allows the reducing-end pyranose ring to remain intact. No carbohydrate protecting groups are needed, and the resulting N-allylglycosylamide can be easily linked to other molecules. Two examples of analogs of silyl Lewis(x) and sulfo Lewis(x) have been derivatized by this process.