摘要
一锅煮合成并表征了2',4"-O-双(三甲基硅)红霉素A9-O-(1-乙氧基-1-甲基乙基)肟,首次在丙酮-水混合溶剂中培养出了单晶.X射线衍射表明,其结构为四方晶系,I4空间群,晶胞参数:a=b=2.9536(1)nm,c=1.4488(1)nm,V=12.63897(4)nm3,Z=8,R=0.068,wR=0.067.对区域选择性影响因素的研究表明:甲基化时溶液浓度应控制0.052和0.067mol/L之间;分别采用了四氢呋喃、二氯甲烷、甲基叔丁基醚、甲苯与二甲亚砜作为混合溶剂进行甲基化反应,发现在甲苯-二甲亚砜中的效果最好,6-OH的甲基化选择性可达到81.69%.
2',4"-O-Bis(trimethylsilyl)erythromycin A 9-O-(1-ethoxy-1-methylethyl)oxime was synthesized in one pot and characterized.The crystal structure of the title compound grown from acetone-water was determined by the single crystal X-ray structure analysis.The crystal belongs to tetragonal system with 14 space group and a=b=2.9536(1)nm,c=1.4488(1)nm,V=12.63897(4)nm^3,Z=8,R=0.068,wR=0.067 for 7266 unique reflections.The research on the regioselectivity has shown that the concentration should be confined within 0.052-0.067 mol/L.Among the candidates of CH2Cl2-DMSO,methyl t-butyl ether-DMSO and toluene-DMSO,toluene-DMSO was the best mixture solvent for methylation with 81.69%selectivity to 6-OH,instead of the original expensive THF-DMSO.
作者
梁建华
姚国伟
LIANG;Jian-Hua;YAO;Guo-Wei(School of Life Science and Technology,Beijing Imstitute of Technology,Beijing 100081)
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2006年第5期676-680,共5页
Chinese Journal of Organic Chemistry
基金
国家经贸委技术创新项目(No.01BK-009)
北京理工大学基础研究基金(No.200506B4223)资助项目.
关键词
克拉霉素
晶体
区域选择性
clarithromycin
crystal
regioselectivity
