2-naphthyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(D-1-carboxyethyl)-β-D-glucopyranoside | 404947-52-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-naphthyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(D-1-carboxyethyl)-β-D-glucopyranoside
• CAS: 404947-52-0
• 化学式: C₂₄H₂₉NO₈
• 分子量: 459.496
• InChiKey: XXKKDQIOYAOEGC-VTKUTBRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  112.55
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-naphthyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(D-1-carboxyethyl)-β-D-glucopyranoside 在 palladium on activated charcoal N-羟基丁二酰亚胺 、 氢气 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 9.0h， 生成 O-(2-naphthyl 2-acetamido-2-deoxy-β-D-glucopyranosid-3-yl)-D-lactoyl-L-alanyl-D-isoglutamine
  参考文献：
  名称：

  摘要：

  Synthesis of N-acetylmuramyl-L-alanyl-D-isoglutamine phenyl and (2-naphthyl) beta -glycosides, novel muramyl dipeptide derivatives with phenolic aglycons, was reported. The starting N-acetylglucosamine aryl glycosides were obtained by glycosylation of phenols with peracetylated alpha -glucosaminyl chloride under the conditions of phase-transfer catalysis and used for the synthesis of 4,6-O-isopropylidene-N-acetylmyramic acid aryl beta -glycosides. Condensation of these derivatives with a dipeptide and subsequent deprotection resulted in the intended glycopeptides.

  DOI：

  10.1023/a:1012940803366
• 作为产物：
  描述：

  2-萘基 2-乙酰氨基-2-脱氧-beta-D-吡喃葡萄糖苷 在 sodium hydride 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 生成 2-naphthyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(D-1-carboxyethyl)-β-D-glucopyranoside
  参考文献：
  名称：

  摘要：

  Synthesis of N-acetylmuramyl-L-alanyl-D-isoglutamine phenyl and (2-naphthyl) beta -glycosides, novel muramyl dipeptide derivatives with phenolic aglycons, was reported. The starting N-acetylglucosamine aryl glycosides were obtained by glycosylation of phenols with peracetylated alpha -glucosaminyl chloride under the conditions of phase-transfer catalysis and used for the synthesis of 4,6-O-isopropylidene-N-acetylmyramic acid aryl beta -glycosides. Condensation of these derivatives with a dipeptide and subsequent deprotection resulted in the intended glycopeptides.

  DOI：

  10.1023/a:1012940803366