1-N-(4-nitrobenzoyl)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine | 18918-52-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-N-(4-nitrobenzoyl)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine
• 英文别名: 4-nitro-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzamide；N-4-Nitrobenzoyl-2,3,4,6-tetra-O-acetyl-β-D-glucosylamin；N-(Tetraacetyl-1-β-D-glucopyranosyl)-4-nitro-benzamid；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(4-nitrobenzoyl)amino]oxan-2-yl]methyl acetate
• CAS: 18918-52-0
• 化学式: C₂₁H₂₄N₂O₁₂
• 分子量: 496.428
• InChiKey: DWIMDJJMKOBINH-GQUPQBGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  189
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  在 水 作用下， 生成 1-N-(4-nitrobenzoyl)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine
  参考文献：
  名称：

  Application of bis(diphenylphosphino)ethane (DPPE) in Staudinger-type N-glycopyranosyl amide synthesis

  摘要：

  Bis(diphenylphosphino)ethane (DPPE) reacts with pyranosyl azides derived from D-glucose and D-glucuronic acid in the presence of acid chlorides to yield the corresponding glycosyl amides. Reaction rates are comparable to those with triphenylphosphine, however, the byproduct phosphine oxide is easily removed from reaction mixtures using column chromatography. The simple and clean workup allows for the formation of collections of related compounds by parallel synthesis, and the method is also applicable to scaled-up reactions. The beta-stereochemistry of the glycosyl azide precursor is retained in all cases, which is supported by X-ray crystallography in several cases. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.02.001

文献信息

• An easy access to anomeric glycosyl amides and imines(Schiff bases) via transformation of glycopyranosyl trimethylphosphinimides
  作者：László Kovács、Erzsébet Ősz、Valéria Domokos、Wolfgang Holzer、Zoltán Györgydeák

  DOI：10.1016/s0040-4020(01)00380-5

  日期：2001.5

  The preparation and application of anomeric glycosyl phosphinimides in preparative synthesis were studied. Starting from the appropriate glycosyl azides and trialkyl or triaryl phosphines, the corresponding phosphinimides were obtained by modified Staudinger reactions. The latter compounds were readily converted into 1-N-acyl-gluco- and galactopyranosyl amines with high yields by applying activated

  研究了异头糖基次膦酰亚胺的制备及在合成中的应用。从合适的糖基叠氮化物和三烷基或三芳基膦开始，通过改良的施陶丁格反应获得相应的亚膦酰亚胺。通过使用活化的酸衍生物或简单的羧酸，后一种化合物容易以高收率转化成1 - N-酰基-葡萄糖-和吡喃半乳糖基胺。通过氮杂-维蒂希反应分别使用脂族或芳族醛，获得1- N-亚烷基-亚芳基次膦酸酯或席夫碱（席夫碱）。
• Synthesis of Glucopyranosyl Amides Using Polymer‐Supported Reagents
  作者：Yuriko Y. Root、Maximillian S. Bailor、Peter Norris

  DOI：10.1081/scc-120039504

  日期：2004.1.1

  Abstract 2,3,4,6‐Tetra‐O‐acetyl‐β‐D‐glucopyranosyl azide reacts efficiently with polymer‐supported triphenylphosphine and various acid chlorides to yield glucopyranosyl amides with retention of the β‐gluco stereochemistry.

  摘要 2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基叠氮化物与聚合物负载的三苯基膦和各种酰氯有效反应，生成保留β-葡萄糖立体化学的吡喃葡萄糖基酰胺。