(9E)-3-O-descladinosylerythromycin A 9-(O-allyloxime) | 863484-37-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (9E)-3-O-descladinosylerythromycin A 9-(O-allyloxime)
• 英文别名: (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-4,7,12,13-tetrahydroxy-3,5,7,9,11,13-hexamethyl-10-prop-2-enoxyimino-oxacyclotetradecan-2-one
• CAS: 863484-37-1
• 化学式: C₃₂H₅₈N₂O₁₀
• 分子量: 630.82
• InChiKey: BXPDITFUEDSVQS-RPOWJCTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  44.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  170.74
• 氢给体数：
  5.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  光气 、 (9E)-3-O-descladinosylerythromycin A 9-(O-allyloxime) 在 吡啶 、 甲醇 、 sodium hydroxide 作用下， 以 二氯甲烷 、 甲苯 、 水 为溶剂， 反应 22.0h， 以91%的产率得到(9E)-N-demethyl-3-O-descladinosylerythromycin A 9-(O-allyloxime) 2',3'-urethane-11,12-carbonate-3,6-diether
  参考文献：
  名称：

  Descladinosyl erythromycin in phosgene-assisted cyclic 3,6-ether formation

  摘要：

  Erythromycin A has been converted into a 3,6-bridged ether via a C-3 chloroformate by nucleophilic addition of the hydroxyl function at C-6. Further transformations afforded N-demethyl-3-O-descladinosylery-thromycin A 2',3'-carbamate-11,12-carbonate-3,6-ether in 59% overall yield over four reaction steps from (9E)-erythromycin A 9-(O-allyloxime). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.118
• 作为产物：
  描述：

  (9E)-erythromycin A 9-(O-allyloxime) 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 1.67h， 以85%的产率得到(9E)-3-O-descladinosylerythromycin A 9-(O-allyloxime)
  参考文献：
  名称：

  Descladinosyl erythromycin in phosgene-assisted cyclic 3,6-ether formation

  摘要：

  Erythromycin A has been converted into a 3,6-bridged ether via a C-3 chloroformate by nucleophilic addition of the hydroxyl function at C-6. Further transformations afforded N-demethyl-3-O-descladinosylery-thromycin A 2',3'-carbamate-11,12-carbonate-3,6-ether in 59% overall yield over four reaction steps from (9E)-erythromycin A 9-(O-allyloxime). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.118

文献信息

• Synthesis and antibacterial activity of new 9-O-arylpropenyloxime ketolides
  作者：Ghilsoo Nam、Yang Soo Kim、Kyung Il Choi

  DOI：10.1016/j.bmcl.2010.01.153

  日期：2010.4

  A novel series of 9-O-arylpropenyloxime ketolide was synthesized and evaluated for their antibacterial activity. This series of ketolide exhibited potent activity against clinically isolated gram-positive strains including Staphylococcus pneumoniae and Straptococcus Pyogenes. (C) 2010 Published by Elsevier Ltd.