2-acetamido-2-deoxy-6-O-(4-methoxybenzyl)-3-O-monochloroacetyl-β-D-glucopyranosyl azide | 147183-80-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-2-deoxy-6-O-(4-methoxybenzyl)-3-O-monochloroacetyl-β-D-glucopyranosyl azide
• CAS: 147183-80-0
• 化学式: C₁₈H₂₃ClN₄O₇
• 分子量: 442.856
• InChiKey: QQQVRKWLADBSIT-JVNHZCFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 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：

  溴2-脱氧-2-N-邻苯二甲酰亚胺基-3,4,6-三-O-乙酰基-alpha,beta-D-吡喃葡萄糖苷 、 2-acetamido-2-deoxy-6-O-(4-methoxybenzyl)-3-O-monochloroacetyl-β-D-glucopyranosyl azide 在 2,4,6-三甲基吡啶 、 silver trifluoromethanesulfonate 作用下， 以 硝基甲烷 为溶剂， 以80%的产率得到2-(O-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-acetimido-2-deoxy-3-O-monochloroacetyl-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
• 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 tetrafluoroboric acid 、 4 A molecular sieve 、 sodium cyanoborohydride 、 三乙胺 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-acetamido-2-deoxy-6-O-(4-methoxybenzyl)-3-O-monochloroacetyl-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