iso-propyl 3,4,6-tri-O-benzyl-2-deoxy-2-(2,4-dinitrophenylamino)-α-D-glucopyranosyl-(1->4)-(methyl 3-O-benzyl-2-O-pivaloyl-α-L-idopyranosyluronate) | 1203584-63-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: iso-propyl 3,4,6-tri-O-benzyl-2-deoxy-2-(2,4-dinitrophenylamino)-α-D-glucopyranosyl-(1->4)-(methyl 3-O-benzyl-2-O-pivaloyl-α-L-idopyranosyluronate)
• 英文别名: methyl (2R,3S,4S,5R,6R)-5-(2,2-dimethylpropanoyloxy)-3-[(2R,3R,4R,5S,6R)-3-(2,4-dinitroanilino)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4-phenylmethoxy-6-propan-2-yloxyoxane-2-carboxylate
• CAS: 1203584-63-7
• 化学式: C₅₅H₆₃N₃O₁₆
• 分子量: 1022.12
• InChiKey: LEAUDUSIWVFIHA-WANXDXHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  74
• 可旋转键数：
  24
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  230
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  iso-propyl (methyl 3-O-benzyl-4-O-levulinoyl-2-O-pivaloyl-L-idopyranosyluronate) 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 一水合肼 、 溶剂黄146 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 iso-propyl 3,4,6-tri-O-benzyl-2-deoxy-2-(2,4-dinitrophenylamino)-β-D-glucopyranosyl-(1->4)-(methyl 3-O-benzyl-2-O-pivaloyl-α-L-idopyranosyluronate) 、 iso-propyl 3,4,6-tri-O-benzyl-2-deoxy-2-(2,4-dinitrophenylamino)-α-D-glucopyranosyl-(1->4)-(methyl 3-O-benzyl-2-O-pivaloyl-α-L-idopyranosyluronate)
  参考文献：
  名称：

  Synthesis of Differentially Protected Glucosamine Building Blocks and Their Evaluation as Glycosylating Agents

  摘要：

  The modular assembly of heparin oligosaccharides requires glucosamine building blocks with amine protecting groups for a-selective glycosylations that can be readily removed. The synthesis of N-4-nitrobenzensulphonamide (nosyl)- and N-2,4-dinitrophenyl (DNP)-protected glucosamine building blocks and their evaluation as glycosylating agents is described. The N-nosyl-protected glucosamine building blocks were challenging to prepare and their glycosylations resulted in inseparable mixtures of products. The N-DNP-protected glucosamines, however, were readily synthesized and resulted in a-selective couplings to protected L-iduronic acid derivatives.

  DOI：

  10.1080/07328300903105108