(R)-(3aS,4R,7R,8S,9S,10R,11R,13R,15R,15aR)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,14-trioxotetradecahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazol-8-yl 2-(benzo[d][1,3]dioxol-4-yl)-4,4-dimethylpyrrolidine-1-carboxylate | 1426540-47-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(3aS,4R,7R,8S,9S,10R,11R,13R,15R,15aR)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,14-trioxotetradecahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazol-8-yl 2-(benzo[d][1,3]dioxol-4-yl)-4,4-dimethylpyrrolidine-1-carboxylate
• 英文别名: [(1S,2R,5R,6S,7S,8R,9R,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-4,12,16-trioxo-3,17-dioxa-15-azabicyclo[12.3.0]heptadecan-6-yl] (2R)-2-(1,3-benzodioxol-4-yl)-4,4-dimethylpyrrolidine-1-carboxylate
• CAS: 1426540-47-7
• 化学式: C₄₅H₆₉N₃O₁₃
• 分子量: 860.055
• InChiKey: JVTGJNFCMDESGV-BFKYQZGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  61
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  181
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  2,2-二甲基琥珀酸 在 甲醇 、 lithium aluminium tetrahydride 、 仲丁基锂 、 三乙胺 、 尿素 、 三氟乙酸 、 鹰爪豆碱 作用下， 以 四氢呋喃 、 甲基叔丁基醚 、 乙酸乙酯 、 异丙醇 、 乙腈 为溶剂， 反应 52.0h， 生成 (R)-(3aS,4R,7R,8S,9S,10R,11R,13R,15R,15aR)-10-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-2,6,14-trioxotetradecahydro-1H-[1]oxacyclotetradecino[4,3-d]oxazol-8-yl 2-(benzo[d][1,3]dioxol-4-yl)-4,4-dimethylpyrrolidine-1-carboxylate
  参考文献：
  名称：

  Novel 3-O-carbamoyl erythromycin A derivatives (carbamolides) with activity against resistant staphylococcal and streptococcal isolates

  摘要：

  A novel series of 3-O-carbamoyl erythromycin A derived analogs, labeled carbamolides, with activity versus resistant bacterial isolates of staphylococci (including macrolide and oxazolidinone resistant strains) and streptococci are reported. An (R)-2-aryl substituent on a pyrrolidine carbamate appeared to be critical for achieving potency against resistant strains. Crystal structures showed a distinct aromatic interaction between the (R)-2-aryl (3-pyridyl for 4d) substituent on the pyrrolidine and G2484 (G2505, Escherichia coli) of the Deinococcus radiodurans 50S ribosome (3.2 angstrom resolution). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.067