4-acetoxy-5-acetylamino-2-{3,4-diacetoxy-5-acetylamino-6-[2-(3-azido-propylcarbamoyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-ethoxy]-tetrahydro-pyran-2-ylmethoxy}-6-(1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester | 914456-69-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-acetoxy-5-acetylamino-2-{3,4-diacetoxy-5-acetylamino-6-[2-(3-azido-propylcarbamoyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-ethoxy]-tetrahydro-pyran-2-ylmethoxy}-6-(1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 914456-69-2
• 化学式: C₅₃H₆₇N₇O₂₃
• 分子量: 1170.15
• InChiKey: YUHYPZFDXMINCN-BJWWYPJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  83.0
• 可旋转键数：
  26.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  395.41
• 氢给体数：
  4.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  4-acetoxy-5-acetylamino-2-{3,4-diacetoxy-5-acetylamino-6-[2-(3-azido-propylcarbamoyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-ethoxy]-tetrahydro-pyran-2-ylmethoxy}-6-(1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 二乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{(2R,3R,4R,5R,6S)-3,4-diacetoxy-5-acetylamino-6-[(S)-2-amino-2-(3-azido-propylcarbamoyl)-ethoxy]-tetrahydro-pyran-2-ylmethoxy}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  A Potentially Valuable Advance in the Synthesis of Carbohydrate-Based Anticancer Vaccines through Extended Cycloaddition Chemistry

  摘要：

  An advance in the long-term problem of joining complex oligosaccharides to polypeptides and even proteins is described herein. The key method involves equipping the oligosaccharide sector with an azide and the polypeptide with pendant alkynyl functionality. The two sectors are joined through a "click-like" cycloaddition. The method encompasses oligosaccharide constructs with several azide linkages which undergo concurrent cycloaddition to peptide-based acetylenes. This technology could well prove to be useful in the construction of fully synthetic vaccines.

  DOI：

  10.1021/jo061406i
• 作为产物：
  描述：

  、 3-叠氮基丙胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以78%的产率得到4-acetoxy-5-acetylamino-2-{3,4-diacetoxy-5-acetylamino-6-[2-(3-azido-propylcarbamoyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-ethoxy]-tetrahydro-pyran-2-ylmethoxy}-6-(1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  A Potentially Valuable Advance in the Synthesis of Carbohydrate-Based Anticancer Vaccines through Extended Cycloaddition Chemistry

  摘要：

  An advance in the long-term problem of joining complex oligosaccharides to polypeptides and even proteins is described herein. The key method involves equipping the oligosaccharide sector with an azide and the polypeptide with pendant alkynyl functionality. The two sectors are joined through a "click-like" cycloaddition. The method encompasses oligosaccharide constructs with several azide linkages which undergo concurrent cycloaddition to peptide-based acetylenes. This technology could well prove to be useful in the construction of fully synthetic vaccines.

  DOI：

  10.1021/jo061406i