phenyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside | 404947-30-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: phenyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
• 英文别名: phenyl 2-(acetylamino)-2-deoxy-4,6-O-(1-methylethylidene)-beta-D-glucopyranoside；N-[(4aR,6S,7R,8R,8aS)-8-hydroxy-2,2-dimethyl-6-phenoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• CAS: 404947-30-4
• 化学式: C₁₇H₂₃NO₆
• 分子量: 337.373
• InChiKey: XONPHWKWCQKCCN-OXGONZEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 在 N-羟基丁二酰亚胺 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 O-(phenyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosid-3-yl)-D-lactoyl-L-alanyl-D-isoglutamine benzyl ester
  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-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 sodium hydroxide 、 苄基三乙基氯化铵 、 sodium methylate 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 为溶剂， 反应 1.0h， 生成 phenyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-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

文献信息

• ——
  作者：A. E. Zemlyakov、V. V. Tsikalov、V. O. Kur'yanov、V. Ya. Chirva、N. V. Bovin

  DOI：10.1023/a:1012940803366

  日期：——

  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.