10-(2-ethoxyprop-2-en-1-yl)-10-desmethylerythralosamine | 900534-12-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 10-(2-ethoxyprop-2-en-1-yl)-10-desmethylerythralosamine
• CAS: 900534-12-5
• 化学式: C₃₃H₅₅NO₉
• 分子量: 609.801
• InChiKey: FDQKSXCZUMOGPE-PQZXAUJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  43.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  116.15
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  10-(2-ethoxyprop-2-en-1-yl)-10-desmethylerythralosamine 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 、 10-(2-oxopropyl)-10-desmethylerythralosamine
  参考文献：
  名称：

  Selective substitutions in the C10-methyl group in erythromycin derivatives

  摘要：

  A method for chemical modifications of the relatively unreactive C10-methyl group in the erythromycin macrolactone ring has been developed. Erythralosamine was protected as an N-oxide in the N,N-dimethylamino group and reacted with NBS in acetic acid to provide two regioisomeric allylic bromides. The same amine was formed from both isomers on nucleophilic substitution. Both regioisomeric bromides in cross-coupling reactions under Stille conditions provided the same product from substitution in the 10-methyl group via a common pi-allylic palladium complex. Under Negishi conditions with trimethylalane, the Pd-catalysed cross-coupling provided the 10-ethyl homologue. X-ray analyses were used to confirm the structure of erythralosamine, and to determine the structures of the allylic bromides from erythralosamine N-oxide. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.098
• 作为产物：
  描述：

  红霉素 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 双氧水 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 58.0h， 生成 10-(2-ethoxyprop-2-en-1-yl)-10-desmethylerythralosamine
  参考文献：
  名称：

  Selective substitutions in the C10-methyl group in erythromycin derivatives

  摘要：

  A method for chemical modifications of the relatively unreactive C10-methyl group in the erythromycin macrolactone ring has been developed. Erythralosamine was protected as an N-oxide in the N,N-dimethylamino group and reacted with NBS in acetic acid to provide two regioisomeric allylic bromides. The same amine was formed from both isomers on nucleophilic substitution. Both regioisomeric bromides in cross-coupling reactions under Stille conditions provided the same product from substitution in the 10-methyl group via a common pi-allylic palladium complex. Under Negishi conditions with trimethylalane, the Pd-catalysed cross-coupling provided the 10-ethyl homologue. X-ray analyses were used to confirm the structure of erythralosamine, and to determine the structures of the allylic bromides from erythralosamine N-oxide. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.098