[(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(1R,5R,7E,9E,11R,12R,14R,18S,19S)-16-[tert-butyl(dimethyl)silyl]oxy-18-methoxy-5,12-dimethyl-11-[(2R,5S,6R)-6-methyl-5-(methylamino)oxan-2-yl]oxy-3-oxo-4,17-dioxabicyclo[12.3.2]nonadeca-7,9-dien-19-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] hex-5-ynoate | 927674-03-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(1R,5R,7E,9E,11R,12R,14R,18S,19S)-16-[tert-butyl(dimethyl)silyl]oxy-18-methoxy-5,12-dimethyl-11-[(2R,5S,6R)-6-methyl-5-(methylamino)oxan-2-yl]oxy-3-oxo-4,17-dioxabicyclo[12.3.2]nonadeca-7,9-dien-19-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] hex-5-ynoate
• CAS: 927674-03-1
• 化学式: C₅₄H₉₂N₂O₁₅Si
• 分子量: 1037.41
• InChiKey: MRZMQIWAGNASND-GKKUCKDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.52
• 重原子数：
  72
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  191
• 氢给体数：
  3
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  4-azido-2,5-dimethoxybenzenesulfonamide 、 [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(1R,5R,7E,9E,11R,12R,14R,18S,19S)-16-[tert-butyl(dimethyl)silyl]oxy-18-methoxy-5,12-dimethyl-11-[(2R,5S,6R)-6-methyl-5-(methylamino)oxan-2-yl]oxy-3-oxo-4,17-dioxabicyclo[12.3.2]nonadeca-7,9-dien-19-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] hex-5-ynoate 在 铜 、 copper(II) sulfate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 27.0h， 以57%的产率得到[(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(1R,5R,7E,9E,11R,12R,14R,18S,19S)-16-[tert-butyl(dimethyl)silyl]oxy-18-methoxy-5,12-dimethyl-11-[(2R,5S,6R)-6-methyl-5-(methylamino)oxan-2-yl]oxy-3-oxo-4,17-dioxabicyclo[12.3.2]nonadeca-7,9-dien-19-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] 4-[1-(2,5-dimethoxy-4-sulfamoylphenyl)triazol-4-yl]butanoate
  参考文献：
  名称：

  Rapid ‘SAR’ via Click Chemistry: An Alkyne-Bearing Spiramycin is fused with Diverse Azides to Yield New Triazole-Antibacterial Candidates

  摘要：

  The spiramycin analogue, 2'-acetyl-4"'-de-N-methyl-4"-O-t-butyldimethylsilylspiramycin I 3,18-(O-t-butyldimethylsilyl)acetal(1), was found to be an adequate antibacterial agent against MRSA strains. An acetylenic sidechain was attached to 1 producing the analog (8), with the core intact but displaying a tethered terminal alkyne, ready for reaction with 19 diverse azides. In the event, the copper-catalyzed Fokin-Huisgen triazole synthesis/coupling gave each of the nineteen new 4"-O-acyl triazole derivatives of 1 in good to nearly quantitative isolated yields.

  DOI：

  10.3987/com-06-s(o)7
• 作为产物：
  描述：

  在 哌啶 作用下， 以 氯仿 为溶剂， 以54%的产率得到[(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(1R,5R,7E,9E,11R,12R,14R,18S,19S)-16-[tert-butyl(dimethyl)silyl]oxy-18-methoxy-5,12-dimethyl-11-[(2R,5S,6R)-6-methyl-5-(methylamino)oxan-2-yl]oxy-3-oxo-4,17-dioxabicyclo[12.3.2]nonadeca-7,9-dien-19-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] hex-5-ynoate
  参考文献：
  名称：

  Rapid ‘SAR’ via Click Chemistry: An Alkyne-Bearing Spiramycin is fused with Diverse Azides to Yield New Triazole-Antibacterial Candidates

  摘要：

  The spiramycin analogue, 2'-acetyl-4"'-de-N-methyl-4"-O-t-butyldimethylsilylspiramycin I 3,18-(O-t-butyldimethylsilyl)acetal(1), was found to be an adequate antibacterial agent against MRSA strains. An acetylenic sidechain was attached to 1 producing the analog (8), with the core intact but displaying a tethered terminal alkyne, ready for reaction with 19 diverse azides. In the event, the copper-catalyzed Fokin-Huisgen triazole synthesis/coupling gave each of the nineteen new 4"-O-acyl triazole derivatives of 1 in good to nearly quantitative isolated yields.

  DOI：

  10.3987/com-06-s(o)7