(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-12,13-dihydroxy-10-hydroxyimino-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclot | 103450-87-9

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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-12,13-dihydroxy-10-hydroxyimino-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclot
• 英文别名: 6-O-Me Ery A 9(E)-oxime；6-O-methyl Ery A 9(Z)-oxime；clarithromycin 9-oxime
• CAS: 103450-87-9；127253-05-8；127253-06-9
• 化学式: C₃₈H₇₀N₂O₁₃
• 分子量: 762.979
• InChiKey: MWBJRTBANFUBOX-LERDGGEFSA-N

物化性质

• 熔点：
  169-171 °C
• 沸点：
  827.7±65.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  53.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  198.43
• 氢给体数：
  5.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (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-12,13-dihydroxy-10-hydroxyimino-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclot 在 sodium disulfide 作用下， 以 乙醇 为溶剂， 以68%的产率得到克拉霉素
  参考文献：
  名称：

  Chemical Modification of Erythromycins. VIII. A New Effective Route to Clarithromycin (6-O-Methylerythromycin A)

  摘要：

  Selective O-methylation of the C-6 hydroxyl group of erythromycin A could be satisfactorily achieved by using its 9-oxime derivatives as the starting materials. Thus, 6-O-methylerythromycin A (clarithromycin) was synthesized from 2'-O,3'-N-bis(benzyloxycarbonyl)-N-demethylerythromycin A via its 9-oxime derivative by 6 steps.

  DOI：

  10.3987/com-90-5616
• 作为产物：
  描述：

  2'-O,3'-N-bis(benzyloxycarbonyl)-N-demethylerythromycin A 9-oxime 在 氢氧化钾 、 甲酸 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 (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-12,13-dihydroxy-10-hydroxyimino-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclot
  参考文献：
  名称：

  Chemical Modification of Erythromycins. VIII. A New Effective Route to Clarithromycin (6-O-Methylerythromycin A)

  摘要：

  Selective O-methylation of the C-6 hydroxyl group of erythromycin A could be satisfactorily achieved by using its 9-oxime derivatives as the starting materials. Thus, 6-O-methylerythromycin A (clarithromycin) was synthesized from 2'-O,3'-N-bis(benzyloxycarbonyl)-N-demethylerythromycin A via its 9-oxime derivative by 6 steps.

  DOI：

  10.3987/com-90-5616

文献信息

• Macrolides Having Antibiotic Activity
  申请人：Yerramilli Murthy V.S.N.

  公开号：US20110071096A1

  公开（公告）日：2011-03-24

  The present invention relates to a semi-synthetic macrolide having antimicrobial activity, in particular antibacterial activity; pharmaceutical compositions comprising the macrolide; and methods of using the macrolide to treat or prevent an infection.

  本发明涉及一种半合成的大环内酯类化合物，具有抗微生物活性，特别是抗细菌活性；药物组合物包括该大环内酯类化合物；以及使用该大环内酯类化合物治疗或预防感染的方法。
• Synthesis and antibacterial activity of O-methyl derivatives of azalide antibiotics: II. 6-OMe derivatives VIA clarithromycin
  作者：Sherman T. Waddell、Gina M. Santorelli、Timothy A. Blizzard、Amy Graham、James Occi

  DOI：10.1016/s0960-894x(98)00227-3

  日期：1998.6

  Direct O-methylation of various derivatives of 9-deoxo-8a- and 9a-aza-8a-homo-erythromycin (2',3'-bis-Cbz protected) gives 6-OMe derivatives only in a small number of special cases. The 6-OMe-azalides can, however, be synthesized beginning from clarithromycin. (C) 1998 Elsevier Science Ltd. All rights reserved.