[(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(3R,5R,6R,7R,9R,11R,12R,13R,14R)-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-12-methylsulfonyloxy-2,4,10-trioxo-oxacyclotetradec-6-yl]oxy]-6-methyloxan-3-yl] acetate | 160145-81-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(3R,5R,6R,7R,9R,11R,12R,13R,14R)-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-12-methylsulfonyloxy-2,4,10-trioxo-oxacyclotetradec-6-yl]oxy]-6-methyloxan-3-yl] acetate
• CAS: 160145-81-3
• 化学式: C₃₃H₅₇NO₁₃S
• 分子量: 707.88
• InChiKey: WRQHFHHTAHXSKE-MSHNGPDTSA-N

物化性质

• 沸点：
  793.7±60.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  48
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  190
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(3R,5R,6R,7R,9R,11R,12R,13R,14R)-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-12-methylsulfonyloxy-2,4,10-trioxo-oxacyclotetradec-6-yl]oxy]-6-methyloxan-3-yl] acetate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 丙酮 为溶剂， 反应 20.0h， 以88%的产率得到(2S,3R,4S,6R)-4-(dimethylamino)-2-(((3R,5R,6R,7R,9R,13S,14R,E)-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-2,4,10-trioxooxacyclotetradec-11-en-6-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl acetate
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Ketolides (6-O-Methyl-3-oxoerythromycin Derivatives):  A New Class of Antibacterials Highly Potent Against Macrolide-Resistant and -Susceptible Respiratory Pathogens

  摘要：

  In the search for new antibiotics active against macrolide-resistant pneumococci and Haemophilus influenzae, we synthesized a new class of 3-oxo-6-O-methylerythromycin derivatives, so-called "ketolides". A keto function was introduced in position 3 after removal of L-cladinose, a sugar which has long been thought essential. Further modifications of the macrolactone backbone allowed us to obtain three different series of 9-oxime, 11,12-carbamate, and 11,12-hydrazonocarbamate ketolides. These compounds were found to be very active against penicillin/erythromycin-resistant pneumococci and noninducers of MLS(B) resistance. The 11,12-substituted ketolide 61 (HMR 3004) demonstrated a potent activity against multiresistant pneumococci associated with a well-balanced activity against all bacteria involved in respiratory infections including H. influenzae, Mycoplasma catarrhalis, group A streptococci, and atypical bacteria. In addition HMR 3004 displayed high therapeutic activity in animals infected by all major strains, irrespective of their resistance phenotype.

  DOI：

  10.1021/jm980240d
• 作为产物：
  描述：

  2'-O-acetyl-6-O-methylerythromycin A 在 吡啶 、 盐酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 [(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(3R,5R,6R,7R,9R,11R,12R,13R,14R)-14-ethyl-13-hydroxy-7-methoxy-3,5,7,9,11,13-hexamethyl-12-methylsulfonyloxy-2,4,10-trioxo-oxacyclotetradec-6-yl]oxy]-6-methyloxan-3-yl] acetate
  参考文献：
  名称：

  A Facile and Scaleable Synthesis of 3-O-Decladinose-6-methyl-10,11-dehydrate-erythromycin-3-one-2‘-acetate, an Important Intermediate for Ketolide Synthesis

  摘要：

  A facile and scaleable synthetic process of compound 2, an important intermediate for synthesis of ketolide semisynthetic antibiotics, was developed starting from commercially available clathromycin with an overall yield of similar to 74%. This synthetic pathway was composed of four steps from compound 3 which could be prepared from clathromycin without using expensive reagents such as EDC, HCl (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride) or more active reagents such as methanesulfonic anhydride. This new process was efficient and practical as demonstrated by scale-up to prepare more than 1 kg of pure compound 2.

  DOI：

  10.1021/op060001x

文献信息

• Erythromycin compounds
  申请人：Roussel Uclaf

  公开号：US05635485A1

  公开（公告）日：1997-06-03

  An erythromycin compound of Formula I or its non-toxic acid addition salt having antibiotic activity.

  具有抗生素活性的式I的红霉素化合物或其非毒性酸加成盐。
• Eryhromycin derivatives
  申请人：Roussel Uclaf

  公开号：US05614614A1

  公开（公告）日：1997-03-25

  Novel intermediates for the preparation of the compounds of Formula I wherein the substituents are as defined in the specification.

  为制备式I化合物中定义的取代基的新型中间体。
• Drug. Future 1998, 23, 591-597
  作者：

  DOI：——

  日期：——