N-acetyl-N-allyl-2-acetamido-2-deoxy-β-D-glucopyranosylamine | 176664-36-1

• 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-β-D-glucopyranosylamine
• 英文别名: N-[(2R,3R,4R,5S,6R)-2-[acetyl(prop-2-enyl)amino]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 176664-36-1
• 化学式: C₁₃H₂₂N₂O₆
• 分子量: 302.327
• InChiKey: NVUWOLNSBKZMND-SYLRKERUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  巯基乙胺 、 N-acetyl-N-allyl-2-acetamido-2-deoxy-β-D-glucopyranosylamine 以 甲醇 为溶剂， 反应 8.0h， 以80%的产率得到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 sodium methylate 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 75.0h， 生成 N-acetyl-N-allyl-2-acetamido-2-deoxy-β-D-glucopyranosylamine
  参考文献：
  名称：

  An Efficient Synthesis of N-Allylglycosylamides from Unprotected Carbohydrates

  摘要：

  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.

  DOI：

  10.1021/jo9522522

文献信息

• Chemoenzymatic Synthesis of Neoglycopeptides:  Application to an α-Gal-Terminated Neoglycopeptide
  作者：Delphine Ramos、Patrick Rollin、Werner Klaffke

  DOI：10.1021/jo001439c

  日期：2001.5.1

  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.
• 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.