2'-O-acetyl-3-O-decladinosyl-9-deoxo-9a-(isopropylcarbamoyl)-9a-aza-9a-homoerythromycin A | 797056-73-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-O-acetyl-3-O-decladinosyl-9-deoxo-9a-(isopropylcarbamoyl)-9a-aza-9a-homoerythromycin A
• CAS: 797056-73-6
• 化学式: C₃₅H₆₅N₃O₁₁
• 分子量: 703.915
• InChiKey: JNHOTMFKOIQQFP-UVQMZFRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  49.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  187.56
• 氢给体数：
  5.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2'-O-acetyl-3-O-decladinosyl-9-deoxo-9a-(isopropylcarbamoyl)-9a-aza-9a-homoerythromycin A 在 三氟乙酸吡啶 、 二甲基亚砜 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 26.5h， 以21%的产率得到
  参考文献：
  名称：

  Novel 9a-carbamoyl- and 9a-thiocarbamoyl-3-decladinosyl-6-hydroxy and 6-methoxy derivatives of 15-membered macrolides

  摘要：

  An efficient method for the synthesis of diverse 9a-carbamoyl- and 9a-thiocarbamoyl-3-decladinosyl-6-hydroxy and 3-decladinosyl-6-methoxy derivatives of 15-membered azalides has been developed. These derivatives bear various alkyl and aryl groups attached to macrolide scaffold through urea or thiourea moieties at 9a position. Chemical transformations of hydroxy group at position C-3 afforded range of ketolides, anhydrolides, herniketals, cyclic ethers, and acylides. It has been shown that 6-hydroxy and 6-methoxy derivatives undergo different chemical transformations under otherwise identical reaction conditions. Antimicrobial properties of prepared compounds were evaluated. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.04.021
• 作为产物：
  描述：

  (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10,13-tetrahydroxy-3,5,8,10,12,14-hexamethyl-15-oxo-N-propan-2-yl-1-oxa-6-azacyclopentadecane-6-carboxamide 、 乙酸酐 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以100%的产率得到2'-O-acetyl-3-O-decladinosyl-9-deoxo-9a-(isopropylcarbamoyl)-9a-aza-9a-homoerythromycin A
  参考文献：
  名称：

  Novel 9a-carbamoyl- and 9a-thiocarbamoyl-3-decladinosyl-6-hydroxy and 6-methoxy derivatives of 15-membered macrolides

  摘要：

  An efficient method for the synthesis of diverse 9a-carbamoyl- and 9a-thiocarbamoyl-3-decladinosyl-6-hydroxy and 3-decladinosyl-6-methoxy derivatives of 15-membered azalides has been developed. These derivatives bear various alkyl and aryl groups attached to macrolide scaffold through urea or thiourea moieties at 9a position. Chemical transformations of hydroxy group at position C-3 afforded range of ketolides, anhydrolides, herniketals, cyclic ethers, and acylides. It has been shown that 6-hydroxy and 6-methoxy derivatives undergo different chemical transformations under otherwise identical reaction conditions. Antimicrobial properties of prepared compounds were evaluated. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.04.021