N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) 1-naphthoic amide | 756517-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) 1-naphthoic amide
• 英文别名: N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1-naphthamide；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(naphthalene-1-carbonylamino)oxan-2-yl]methyl acetate
• CAS: 756517-38-1
• 化学式: C₂₅H₂₇NO₁₀
• 分子量: 501.49
• InChiKey: WYXNQAMHGMVXON-MXCHMSEPSA-N

物化性质

• 熔点：
  138-140 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  652.4±55.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) 1-naphthoic amide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以75%的产率得到N-(β-D-glucopyranosyl) 1-naphthoic amide
  参考文献：
  名称：

  Amide-1,2,3-triazole bioisosterism: the glycogen phosphorylase case

  摘要：

  Per-O-acetylated beta-D-glucopyranosyl azide was transformed into an intermediate iminophosphorane by PMe3 which was then acylated to N-acyl-beta-D-glucopyranosylamines. The same azide and substituted acetylenes gave 1-(beta-D-glucopyranosyl)-4-substituted-1,2,3-triazoles in Cu(I)-catalyzed azide-alkyne cycloadditions. Deprotection of these products by the Zemplen method furnished beta-D-Glc(p)-NHCO-R derivatives as well as 1-(beta-D-Glc(p))-4-R-1,2,3-triazoles which were evaluated as inhibitors of rabbit muscle glycogen phosphorylase b. Pairs of amides versus triazoles with the same R group displayed similar inhibition constants. X-ray crystallographic studies on the enzyme-inhibitor complexes revealed high similarities in the binding of pairs with R = 2-naphthyl and hydroxymethyl, while for the R = Ph and 1-naphthyl compounds a different orientation of the aromatic part and changes in the conformation of the 280s loop were observed. By this study new examples of amide-1,2,3-triazole bioisosteric relationship have been provided. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.03.021
• 作为产物：
  描述：

  1-萘甲酰氯 、 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 在 PPh₃-polymer supported 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) 1-naphthoic amide
  参考文献：
  名称：

  使用聚合物负载的试剂合成吡喃葡萄糖基酰胺

  摘要：

  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。

  DOI：

  10.1081/scc-120039504

文献信息

• Synthesis of N-(β-D-glucopyranosyl)- and N-(2-acetamido-2-deoxy-β-D-glucopyranosyl) amides as inhibitors of glycogen phosphorylase
  作者：Zoltán Györgydeák、Zsuzsa Hadady、Nóra Felföldi、Attila Krakomperger、Veronika Nagy、Marietta Tóth、Attila Brunyánszki、Tibor Docsa、Pál Gergely、László Somsák

  DOI：10.1016/j.bmc.2004.07.013

  日期：2004.9

  2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl- and 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl azides were transformed into the corresponding per-O-acetylated N-(beta-D-glycopyranosyl) amides via a PMe3 mediated Staudinger protocol (generation of N-(beta-D-glycopyranosyl)imino-trimethylphosphoranes followed by acylation with carboxylic acids, acid chlorides or anhydrides). The deprotected compounds obtained by Zemplen deacetylation were evaluated as inhibitors of rabbit muscle glycogen phosphorylase b. The best inhibitor of this series has been N-(beta-D-glucopyranosyl) 3-(2-naphthyl)-propenoic amide (K-i = 3.5 muM). (C) 2004 Elsevier Ltd. All rights reserved.
• Application of bis(diphenylphosphino)ethane (DPPE) in Staudinger-type N-glycopyranosyl amide synthesis
  作者：David P. Temelkoff、Craig R. Smith、Daniel A. Kibler、Shawn McKee、Sara J. Duncan、Matthias Zeller、Mo Hunsen、Peter Norris

  DOI：10.1016/j.carres.2006.02.001

  日期：2006.7

  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.