[(2R,3R,4S,5R,6S)-6-Methoxy-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yl]-methanol | 157487-11-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2R,3R,4S,5R,6S)-6-Methoxy-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yl]-methanol
• CAS: 157487-11-1
• 化学式: C₂₄H₃₂O₇
• 分子量: 432.514
• InChiKey: NRCQPKNIBIIAPD-IGCYBFCNSA-N

物化性质

• 沸点：
  558.6±50.0 °C(predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6S)-6-Methoxy-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yl]-methanol 在 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 (2S,3R,4S,5S,6R)-2-Methoxy-5-methoxymethyl-6-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：

  一氧化碳 、 (2R,3R,4R,5R,6S)-3-Iodo-6-methoxy-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran 在 偶氮二异丁腈 、 三苯基氢化锗 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 苯 为溶剂， 105.0 ℃ 、9.65 MPa 条件下， 反应 12.0h， 生成 [(2R,3R,4S,5R,6S)-6-Methoxy-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yl]-methanol
  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