Quinoxaline-2-carboxylic acid 2-[(2S,4R,5R,6R)-5-[(2R,4R,5S,6R)-4-azido-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-ethyl ester | 729592-66-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Quinoxaline-2-carboxylic acid 2-[(2S,4R,5R,6R)-5-[(2R,4R,5S,6R)-4-azido-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-ethyl ester
• CAS: 729592-66-9
• 化学式: C₃₅H₅₇N₅O₈Si₂
• 分子量: 732.037
• InChiKey: XEDNPIWFLPHLJQ-UPNYAHSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.92
• 重原子数：
  50.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  156.22
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Quinoxaline-2-carboxylic acid 2-[(2S,4R,5R,6R)-5-[(2R,4R,5S,6R)-4-azido-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-ethyl ester 在 水 、 氟化氢吡啶 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 27.0h， 生成
  参考文献：
  名称：

  The significant effect of the carbohydrate structures on the DNA photocleavage of the quinoxaline–carbohydrate hybrids

  摘要：

  The novel DNA interactive quinoxaline-carbohydrate hybrids possessing disaccharides as the carbohydrate moieties were designed and synthesized, and their DNA photocleaving abilities were evaluated in order to examine the effect of the disaccharide structures. The configurations of the glycosidic bonds in the disaccharide strongly affected the DNA photocleaving ability, and two P-glycosidic bond linkages were very effective for the DNA photocleavage. Furthermore, the quinoxaline-disaccharide hybrids exhibited selective cytotoxicity against cancer cells with photoirradiation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.065
• 作为产物：
  描述：

  (2R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol 在 N-溴代丁二酰亚胺(NBS) 、 molecular sieve 、 三氟甲磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.67h， 生成 Quinoxaline-2-carboxylic acid 2-[(2S,4R,5R,6R)-5-[(2R,4R,5S,6R)-4-azido-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-ethyl ester
  参考文献：
  名称：

  The significant effect of the carbohydrate structures on the DNA photocleavage of the quinoxaline–carbohydrate hybrids

  摘要：

  The novel DNA interactive quinoxaline-carbohydrate hybrids possessing disaccharides as the carbohydrate moieties were designed and synthesized, and their DNA photocleaving abilities were evaluated in order to examine the effect of the disaccharide structures. The configurations of the glycosidic bonds in the disaccharide strongly affected the DNA photocleaving ability, and two P-glycosidic bond linkages were very effective for the DNA photocleavage. Furthermore, the quinoxaline-disaccharide hybrids exhibited selective cytotoxicity against cancer cells with photoirradiation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.065