2',4''-O-bistrimethylsilyl erythromycin A 9-O-(2-pyrimydyl)oxime | 930287-47-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2',4''-O-bistrimethylsilyl erythromycin A 9-O-(2-pyrimydyl)oxime
• 英文别名: (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-6-methyl-3-trimethylsilyloxyoxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-4-methoxy-4,6-dimethyl-5-trimethylsilyloxyoxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-10-pyrimidin-2-yloxyimino-oxacyclotetradecan-2-one
• CAS: 930287-47-1
• 化学式: C₄₇H₈₆N₄O₁₃Si₂
• 分子量: 971.39
• InChiKey: ITTJSTADUCBTLP-HYHMCHNFSA-N

物化性质

• 熔点：
  150-152 °C
• 沸点：
  875.7±75.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.16
• 重原子数：
  66
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  202
• 氢给体数：
  3
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  2',4''-O-bistrimethylsilyl erythromycin A 9-O-(2-pyrimydyl)oxime 在 氢氧化钾 、 甲酸 、 sodium hydrogensulfite 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 8.0h， 生成 克拉霉素
  参考文献：
  名称：

  Preparation of clarithromycin. Selective 6-O-methylation of the novel erythromycin A 9-O-(2-pyrimidyl)oxime

  摘要：

  A new method for the preparation of clarithromycin is described through the highly regioselective O-methylation at C(6)-OH of the novel derivative 9-pyrimidyloxime erythromycin A. The facile synthesis of 6,11-O-dimethyl- and 6,11,12-O-trimethyl erythromycin A is also reported. These compounds are useful as standards to assess clarithromycin purity in quality control processes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.124
• 作为产物：
  描述：

  erythromycin A (9E)-oxime hydrochloride 在 potassium tert-butylate 、 三甲基硅咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 2',4''-O-bistrimethylsilyl erythromycin A 9-O-(2-pyrimydyl)oxime
  参考文献：
  名称：

  Preparation of clarithromycin. Selective 6-O-methylation of the novel erythromycin A 9-O-(2-pyrimidyl)oxime

  摘要：

  A new method for the preparation of clarithromycin is described through the highly regioselective O-methylation at C(6)-OH of the novel derivative 9-pyrimidyloxime erythromycin A. The facile synthesis of 6,11-O-dimethyl- and 6,11,12-O-trimethyl erythromycin A is also reported. These compounds are useful as standards to assess clarithromycin purity in quality control processes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.124

文献信息

• Preparation of clarithromycin. Selective 6-O-methylation of the novel erythromycin A 9-O-(2-pyrimidyl)oxime
  作者：Ernesto Brunet、Dulce María Muñoz、Francisco Parra、Susana Mantecón、Olga Juanes、Juan Carlos Rodríguez-Ubis、Ma Carmen Cruzado、Ramón Asensio

  DOI：10.1016/j.tetlet.2006.12.124

  日期：2007.2

  A new method for the preparation of clarithromycin is described through the highly regioselective O-methylation at C(6)-OH of the novel derivative 9-pyrimidyloxime erythromycin A. The facile synthesis of 6,11-O-dimethyl- and 6,11,12-O-trimethyl erythromycin A is also reported. These compounds are useful as standards to assess clarithromycin purity in quality control processes. (c) 2007 Elsevier Ltd. All rights reserved.