(2R,3R,4S,6S)-6-(((ethoxycarbonyl)amino)oxy)-2-methyltetrahydro-2H-pyran-3,4-diyl bis(4-methoxybenzoate) | 157487-15-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,6S)-6-(((ethoxycarbonyl)amino)oxy)-2-methyltetrahydro-2H-pyran-3,4-diyl bis(4-methoxybenzoate)
• CAS: 157487-15-5
• 化学式: C₂₅H₂₉NO₁₀
• 分子量: 503.506
• InChiKey: ZAPHKLVGFBSDHU-NSEXGNSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  127.85
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,6S)-6-(((ethoxycarbonyl)amino)oxy)-2-methyltetrahydro-2H-pyran-3,4-diyl bis(4-methoxybenzoate) 在 六甲基磷酰三胺 、 sodium hydroxide 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (2R,3S,4S,6S)-6-[N-((2R,3S,4S,5R,6S)-5-Benzyloxy-4-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)aminooxy]-2-methyl-tetrahydro-pyran-3,4-diol
  参考文献：
  名称：

  Analysis of Hydroxylamine Glycosidic Linkages: Structural Consequences of the NO Bond in Calicheamicin

  摘要：

  The antitumor activity of calicheamicin is related to its ability to bind to and cleave double-stranded DNA. There is substantial evidence that the oligosaccharide-aryl tail of calicheamicin plays a critical role in the binding selectivity. The calicheamicin oligosaccharide contains some unusual structural elements that may be related to the DNA binding function. A better understanding of how structure is related to function in the calicheamicin oligosaccharide could result in an ability to design new DNA binders. In this paper, the influence of the hydroxylamine glycosidic linkage on the shape of the calicheamicin oligosaccharide is analyzed in detail using a combination of experimental data and molecular mechanics calculations. As part of this work, parameters for N-O bonds have been developed for use with the program DISCOVER (AMBER force field). The analysis indicates that the unusual N-O bond in calicheamicin, with its distinctive torsion angle preferences, organizes the two halves of the molecule into a shape that complements the shape Of the minor groove.

  DOI：

  10.1021/ja00087a005
• 作为产物：
  描述：

  N-羟基氨基甲酸乙酯 、 2,6-dideoxy-3,4-O-bis(4-methoxybenzoyl)allose sulfoxide 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 作用下， 生成 (2R,3R,4S,6S)-6-(((ethoxycarbonyl)amino)oxy)-2-methyltetrahydro-2H-pyran-3,4-diyl bis(4-methoxybenzoate)
  参考文献：
  名称：

  Analysis of Hydroxylamine Glycosidic Linkages: Structural Consequences of the NO Bond in Calicheamicin

  摘要：

  The antitumor activity of calicheamicin is related to its ability to bind to and cleave double-stranded DNA. There is substantial evidence that the oligosaccharide-aryl tail of calicheamicin plays a critical role in the binding selectivity. The calicheamicin oligosaccharide contains some unusual structural elements that may be related to the DNA binding function. A better understanding of how structure is related to function in the calicheamicin oligosaccharide could result in an ability to design new DNA binders. In this paper, the influence of the hydroxylamine glycosidic linkage on the shape of the calicheamicin oligosaccharide is analyzed in detail using a combination of experimental data and molecular mechanics calculations. As part of this work, parameters for N-O bonds have been developed for use with the program DISCOVER (AMBER force field). The analysis indicates that the unusual N-O bond in calicheamicin, with its distinctive torsion angle preferences, organizes the two halves of the molecule into a shape that complements the shape Of the minor groove.

  DOI：

  10.1021/ja00087a005