(4R,5S)-4-bromomethyl-5-(5-hydroxypentyl)-2,2-dimethyl-1,3-dioxolane | 1247028-47-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5S)-4-bromomethyl-5-(5-hydroxypentyl)-2,2-dimethyl-1,3-dioxolane
• CAS: 1247028-47-2
• 化学式: C₁₁H₂₁BrO₃
• 分子量: 281.19
• InChiKey: ZESNTCFGSAHPJD-UWVGGRQHSA-N

反应信息

• 作为反应物：
  描述：

  (4R,5S)-4-bromomethyl-5-(5-hydroxypentyl)-2,2-dimethyl-1,3-dioxolane 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 以94%的产率得到5-[(4S,5R)-5-(bromomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]pentanoic acid
  参考文献：
  名称：

  Toward the Macrocidins: Macrocyclization via Williamson Etherification of a Phenolate

  摘要：

  The synthesis of macrocyclic 3-acyltetramic acids which are immediate precursors of the fungal herbicide macro-cidin A (1) is reported. The crucial closure of the macrocycle was achieved in excellent yield by an unprecedented Williamson etherification of an omega-bromo phenolate generated in situ by a Pd-mediated O-deallylation.

  DOI：

  10.1021/jo101416x
• 作为产物：
  描述：

  (4R,5S)-4-(bromomethyl)-5-[5-(4-methoxybenzyloxy)pentyl]-2,2-dimethyl-1,3-dioxolane 在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以77%的产率得到(4R,5S)-4-bromomethyl-5-(5-hydroxypentyl)-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Toward the Macrocidins: Macrocyclization via Williamson Etherification of a Phenolate

  摘要：

  The synthesis of macrocyclic 3-acyltetramic acids which are immediate precursors of the fungal herbicide macro-cidin A (1) is reported. The crucial closure of the macrocycle was achieved in excellent yield by an unprecedented Williamson etherification of an omega-bromo phenolate generated in situ by a Pd-mediated O-deallylation.

  DOI：

  10.1021/jo101416x