2-acetamido-3-O-acetyl-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl azide | 147157-96-8

• 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: 2-acetamido-3-O-acetyl-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl azide
• 英文别名: 2-acetamido-2-deoxy-3-O-acetyl-6-O-p-methoxybenzyl-β-D-glucopyranosyl azide
• CAS: 147157-96-8
• 化学式: C₁₈H₂₄N₄O₇
• 分子量: 408.411
• InChiKey: RMYCSKGRALKCIO-DUQPFJRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  152.08
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-acetamido-3-O-acetyl-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl azide 在 吡啶 、 ammonium cerium(IV) nitrate 、 silica gel 作用下， 以 水 、 乙腈 为溶剂， 反应 80.0h， 生成 2-acetamido-3,4-di-O-acetyl-2-deoxy-β-D-glucopyranosyl azide
  参考文献：
  名称：

  Stereoselective synthesis of glycosides and anomeric azides of glucosamine

  摘要：

  The beta-azide of O-acetyl protected N-acetyl glucosamine is efficiently accessible via a phase-transfer-catalyzed reaction of the corresponding glycosyl chloride with sodium azide. The azido group revealed to be a useful anomeric protection for modifications of the protecting group pattern of the glucosamine unit. Exchange of the O-acyl groups by 4-methoxybenzylidene and 4-methoxybenzyl (Mpm) protection delivered regioselectively blocked glucosaminyl azide derivatives. In contrast, the N-phthaloyl protected glucosaminyl azide was obtained quantitatively from the corresponding glycosyl fluoride via a boron trifluoride-promoted reaction with trimethylsilyl azide. N-Phthaloyl glucosaminyl fluoride was also revealed to be useful in the synthesis of beta-glucosamine glycosides and saccharides. Chitobiosyl azide 21 carrying a selectively removable 6-O-Mpm protection was synthesized from the O-acetyl protected N-phthaloyl glucosaminyl bromide and N-acetylglucosaminyl azide 13 as an acceptor selectively deblocked at O-4.

  DOI：

  10.1002/prac.19923340705
• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-beta-d-吡喃葡萄糖叠氮化物 在 吡啶 、 tetrafluoroboric acid 、 4 A molecular sieve 、 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 2-acetamido-3-O-acetyl-2-deoxy-6-O-(4-methoxybenzyl)-β-D-glucopyranosyl azide
  参考文献：
  名称：

  Stereoselective synthesis of glycosides and anomeric azides of glucosamine

  摘要：

  The beta-azide of O-acetyl protected N-acetyl glucosamine is efficiently accessible via a phase-transfer-catalyzed reaction of the corresponding glycosyl chloride with sodium azide. The azido group revealed to be a useful anomeric protection for modifications of the protecting group pattern of the glucosamine unit. Exchange of the O-acyl groups by 4-methoxybenzylidene and 4-methoxybenzyl (Mpm) protection delivered regioselectively blocked glucosaminyl azide derivatives. In contrast, the N-phthaloyl protected glucosaminyl azide was obtained quantitatively from the corresponding glycosyl fluoride via a boron trifluoride-promoted reaction with trimethylsilyl azide. N-Phthaloyl glucosaminyl fluoride was also revealed to be useful in the synthesis of beta-glucosamine glycosides and saccharides. Chitobiosyl azide 21 carrying a selectively removable 6-O-Mpm protection was synthesized from the O-acetyl protected N-phthaloyl glucosaminyl bromide and N-acetylglucosaminyl azide 13 as an acceptor selectively deblocked at O-4.

  DOI：

  10.1002/prac.19923340705

文献信息

• Solid-Phase Synthesis of Thioether-Linked Glycopeptide Mimics for Application to Glycoprotein Semisynthesis
  作者：Derek Macmillan、Alison M. Daines、Monika Bayrhuber、Sabine L. Flitsch

  DOI：10.1021/ol025627w

  日期：2002.5.1

  [reaction: see text]. Glycoproteins are particularly suited to protein semisynthesis since homogeneous samples for biological analyses are not readily available using traditional recombinant techniques. Here we apply glycosyl iodoacetamides, normally used for the modification of bacterially derived proteins, to solid-phase glycopeptide synthesis. This provides access to glycopeptide alpha-thioesters

  [反应：请参见文字]。糖蛋白特别适合蛋白质半合成，因为使用传统的重组技术不容易获得用于生物学分析的均质样品。在这里，我们将通常用于修饰细菌衍生蛋白的糖基碘乙酰胺应用于固相糖肽合成。这提供了糖肽α-硫酯的途径，这可能有助于半合成N-连接的糖蛋白模拟物和新型糖肽文库。
• Synthesis of ?-fucosyl glycosides and disaccharides using 4-methoxybenzyl (Mpm) protected fucosyl donors
  作者：Horst Kunz、Carlo Unverzagt

  DOI：10.1002/prac.19923340706

  日期：——

  The 4-methoxybenzyl (Mpm) group removable by selective oxidation was applied as a non-neighbouring-group-active protection of fucose hydroxy functions in the stereoselective synthesis of alpha-fucosides of acceptors containing double bonds sensitive to hydrogenation. With this aim, the synthesis of the alpha-fucosyl chloride (4) carrying the acid-sensitive Mpm protection was elaborated.