N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) 2-naphthoic amide | 756517-35-8

• 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: N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) 2-naphthoic amide
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(naphthalene-2-carbonylamino)oxan-2-yl]methyl acetate
• CAS: 756517-35-8
• 化学式: C₂₅H₂₇NO₁₀
• 分子量: 501.49
• InChiKey: SABSYVJZUVFXIM-MXCHMSEPSA-N

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) 2-naphthoic amide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以92%的产率得到N-(β-D-glucopyranosyl) 2-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：

  2-萘甲酸 、 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 在 三甲基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 以62%的产率得到N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) 2-naphthoic amide
  参考文献：
  名称：

  Synthesis of N-(β-D-glucopyranosyl)- and N-(2-acetamido-2-deoxy-β-D-glucopyranosyl) amides as inhibitors of glycogen phosphorylase

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2004.07.013

文献信息

• 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。