Losigamone, ADD-137022, AO-33
氯西加酮Chemical Name: (5R*)-5-[(alphaS*)-o-Chloro-alpha-hydroxybenzyl]-4-methoxy-2(5H)-furanone; threo-5-(2-Chloro-alpha-hydroxybenzyl)-4-methoxy-2,5-dihydrofuran-2-one; (R*,S*)-(?-5-[(2-Chlorophenyl)hydroxymethyl]-4-methoxy-2(5H)-furanone
CAS No. 112856-44-7
项目整合开发状态: Phase III
项目研究机构: Schwabe (Originator)
合成路线:Condensation of 2-chlorobenzaldehyde (I) with methyl 3-methoxy-2(E)-butenoate (II) in the presence of a strong base in dimethyl sulfoxide/water affords,after acidification and reesterification by ethyl bromide/potassium carbonate ethyl 5-(2-chlorophenyl)-3-methyl-2(E),4(E)-pentadienoate (III).Osmium tetroxide catalyzed dihydroxylation of (III) in acetone/water with N-methylmorpholine-N-oxide (NMO) as cooxidant exclusively yields ethyl 5-(2-chlorophenyl)-4,5-threo-dihydroxy-3-methoxy-2(E)-pentenoate (IV),which in acidic medium spontaneously lactonizes to give the parent compound.
📌 参考资料/链接：
参考文献标题:5-Arylalkyl-4-alkoxy-2(5H)-furanone derivs.,intermediates and process for their preparation as well as use as therapeutic agents
文献作者:Chatterjee,S.S.; Klessing,K.(Willmar Schwabe GmbH)
参考来源:DE 3615157; EP 0247320; JP 1988022087; US 4855320
📄 详细内容
合成路线:Condensation of 2-chlorobenzaldehyde (I) with methyl 3-methoxy-2(E)-butenoate (II) in the presence of a strong base in dimethyl sulfoxide/water affords,after acidification and reesterification by ethyl bromide/potassium carbonate ethyl 5-(2-chlorophenyl)-3-methyl-2(E),4(E)-pentadienoate (III).Osmium tetroxide catalyzed dihydroxylation of (III) in acetone/water with N-methylmorpholine-N-oxide (NMO) as cooxidant exclusively yields ethyl 5-(2-chlorophenyl)-4,5-threo-dihydroxy-3-methoxy-2(E)-pentenoate (IV),which in acidic medium spontaneously lactonizes to give the parent compound.
参考文献标题:LOSIGAMONE < Prop INN >
文献作者:N鰈dner,M.; Chatterjee,S.S.
参考来源:Drugs Fut 1990,15(10),995
产品链接: CAS No. 112856-44-7››