GI-448
Chemical Name: 4''-O-Acetylerythromycin A 9-[O-(3-cyclohexylpropyl)oxime]
CAS No. 301197-85-3
项目整合开发状态: Preclinical
项目研究机构: Abbott (Originator)
合成路线:The title erythromycin O-(phenoxypropyl)oxime was prepared by alkylation of the known erythromycin A 9-oxime (I) with 3-phenoxypropyl bromide (II) under phase-transfer conditions in the presence of KOH and tetrabutylammonium iodide in THF.
合成路线:The reaction of erythromycin A (I) with hydroxylamine in pyridine gives the corresponding oxime (II),which is alkylated with 3-cyclohexylpropyl bromide (III),KOH and tetrabutylammonium iodide in THF to yield the O-alkylated oxime (IV).The reaction of (IV) with Ac2O in pyridine affords the diacetoxyerythromycin A (V),which is finally selectively monodeacetylated in methanol at room temperature to provide the target 4''-O-acetyl derivative.
📌 参考资料/链接：
参考文献标题:Erythromycin derivs.
文献作者:Yoshida,T.; Narita,K.; Kato,H.; Kado,N.; Nishimoto,A.(Hokuriku Seiyaku Co.,Ltd.)
参考来源:EP 1167375; JP 2000351794; WO 0061593
📄 详细内容
合成路线:The reaction of erythromycin A (I) with hydroxylamine in pyridine gives the corresponding oxime (II),which is alkylated with 3-cyclohexylpropyl bromide (III),KOH and tetrabutylammonium iodide in THF to yield the O-alkylated oxime (IV).The reaction of (IV) with Ac2O in pyridine affords the diacetoxyerythromycin A (V),which is finally selectively monodeacetylated in methanol at room temperature to provide the target 4''-O-acetyl derivative.
参考文献标题:Discovery and SAR of macrolide agents with potent activities against Mycobacterium avium-complex
文献作者:Yoshida,T.; Kato,H.; Nishimoto,A.; Watanabe,Y.; Okezaki,E.; Takahashi,U.; Nagata,O.; Yoshizume,S.
参考来源:41st Intersci Conf Antimicrob Agents Chemother (Dec 16 2001,Chicago) 2001,Abst F-1176