carbonic acid benzyl ester 4-(benzyloxycarbonyl-methyl-amino)-2-(4-ethyl-14-hydroxyimino-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,8-trioxo-dodecahydro-1,3,5-trioxa-cyclopentacyclotetradecen-10-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester | 869317-73-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: carbonic acid benzyl ester 4-(benzyloxycarbonyl-methyl-amino)-2-(4-ethyl-14-hydroxyimino-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,8-trioxo-dodecahydro-1,3,5-trioxa-cyclopentacyclotetradecen-10-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester
• CAS: 869317-73-7
• 化学式: C₄₆H₆₂N₂O₁₅
• 分子量: 883.003
• InChiKey: VCEIMTNNHDIFSM-MHZHIXQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.23
• 重原子数：
  63.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  204.25
• 氢给体数：
  1.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  carbonic acid benzyl ester 4-(benzyloxycarbonyl-methyl-amino)-2-(4-ethyl-14-hydroxyimino-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,8-trioxo-dodecahydro-1,3,5-trioxa-cyclopentacyclotetradecen-10-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester 、 聚合甲醛 在 palladium dihydroxide acetate buffer 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以88%的产率得到(1R,2R,5R,7R,8R,9R,11R,12E,13S,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-12-hydroxyimino-9-methoxy-1,5,7,9,11,13-hexamethyl-3,15,17-trioxabicyclo[12.3.0]heptadecane-4,6,16-trione
  参考文献：
  名称：

  9-Oxime-3-ketolides: Modification at the C-11,12-diol moiety and antibacterial activities against key respiratory pathogens

  摘要：

  In the search for new types of ketolide antibiotics active against key respiratory pathogens including erythromycin-resistant strains, we conducted an extensive study on the modification at the C-11,12-diol moiety of 9-oxime-3-ketolide derivatives. Among the derivatives prepared, compound 6 with carbonate at the C-11, 12 position was found to have potent antibacterial activities against erythromycin-resistant Staphylococcus aureus as well as other erythromycin-susceptible strains. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.06.003
• 作为产物：
  描述：

  benzyl [(2S,3R,4S,6R)-2-[[(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2-oxo-10-prop-2-enoxyimino-oxacyclotetradec-6-yl]oxy]-6-methyl-4-[methyl(phenylmethoxycarbonyl)amino]oxan-3-yl] carbonate 在 palladium diacetate 吡啶 、 盐酸 、 甲酸 、 二甲基亚砜 、 三乙胺 、 三苯基膦 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 carbonic acid benzyl ester 4-(benzyloxycarbonyl-methyl-amino)-2-(4-ethyl-14-hydroxyimino-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,8-trioxo-dodecahydro-1,3,5-trioxa-cyclopentacyclotetradecen-10-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  9-Oxime-3-ketolides: Modification at the C-11,12-diol moiety and antibacterial activities against key respiratory pathogens

  摘要：

  In the search for new types of ketolide antibiotics active against key respiratory pathogens including erythromycin-resistant strains, we conducted an extensive study on the modification at the C-11,12-diol moiety of 9-oxime-3-ketolide derivatives. Among the derivatives prepared, compound 6 with carbonate at the C-11, 12 position was found to have potent antibacterial activities against erythromycin-resistant Staphylococcus aureus as well as other erythromycin-susceptible strains. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.06.003