3-bromo-4-methyl-7-((triisopropylsilyl)oxy)-2H-chromen-2-one | 848850-51-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-bromo-4-methyl-7-((triisopropylsilyl)oxy)-2H-chromen-2-one
• 英文别名: 3-Bromo-4-methyl-7-triisopropylsilanyloxy-chromen-2-one
• CAS: 848850-51-1
• 化学式: C₁₉H₂₇BrO₃Si
• 分子量: 411.411
• InChiKey: CXMUEYYJLAWEIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  39.44
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-bromo-4-methyl-7-((triisopropylsilyl)oxy)-2H-chromen-2-one 在 盐酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 Acetic acid (2R,3S,4R,5R,6S)-2-acetoxymethyl-5-azido-3-benzyloxy-6-(3-bromo-4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  α:β Selectivity in the synthesis of 3-substituted, 4-methyl umbelliferone glycosides of N-acetyl glucosamine and chitobiose

  摘要：

  The influence of phenolic acceptor nucleophilicity; for example, 3-substituted, 4-methylumbelliferones, and glycosyl donor electrophilicity; for example, 3- and 4-substituted N-acetylglucosamines, on glycosylation stereochemistry has been evaluated. In a systematic comparison, the stereochemical outcome as well as the reaction yield appeared to be influenced by the 3- and 4-substituents of the donor as well as the 3-substituent of the aryl acceptor. In the context of synthesizing a fluorogenic substrate for oligosaccharyltransferase, an alpha-glycoside was desired. Although most acceptor-donor pairs led to predominantly or exclusively the beta-glycoside, reaction of the most activated (3,4-di-O-benzyl) donor and the least nucleophilic acceptor (3-Br), resulted in a 1:1 ratio of alpha,beta arylglycosides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.053
• 作为产物：
  描述：

  7-triisopropylsilyloxy-4-methylcoumarin 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 26.0h， 以99%的产率得到3-bromo-4-methyl-7-((triisopropylsilyl)oxy)-2H-chromen-2-one
  参考文献：
  名称：

  α:β Selectivity in the synthesis of 3-substituted, 4-methyl umbelliferone glycosides of N-acetyl glucosamine and chitobiose

  摘要：

  The influence of phenolic acceptor nucleophilicity; for example, 3-substituted, 4-methylumbelliferones, and glycosyl donor electrophilicity; for example, 3- and 4-substituted N-acetylglucosamines, on glycosylation stereochemistry has been evaluated. In a systematic comparison, the stereochemical outcome as well as the reaction yield appeared to be influenced by the 3- and 4-substituents of the donor as well as the 3-substituent of the aryl acceptor. In the context of synthesizing a fluorogenic substrate for oligosaccharyltransferase, an alpha-glycoside was desired. Although most acceptor-donor pairs led to predominantly or exclusively the beta-glycoside, reaction of the most activated (3,4-di-O-benzyl) donor and the least nucleophilic acceptor (3-Br), resulted in a 1:1 ratio of alpha,beta arylglycosides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.053