C-75
3-呋兰羧酸,四氢-4-甲基-2-辛基-5-氧-,(2R,3R)-rel- C75反式 Chemical Name: 4-Methylene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid
CAS No. 191282-49-2 (cis-isomer), 191282-48-1 (trans-isomer)
项目整合开发状态: Preclinical
项目研究机构: Johns Hopkins University (Originator), Fasgen (Licensee)
合成路线:p-Methoxybenzyl itaconate (III) was prepared by reaction of itaconic anhydride (I) with p-methoxybenzyl alcohol (II) at 55-60 C (1).Condensation of the lithium enolate of (III) with nonanal (IV) in THF at -78 C gave adduct (V),which upon treatment with trifluoroacetic acid underwent cyclization and benzyl ester deprotection to yield the corresponding butyrolactone as a diastereomeric mixture.The major trans isomer was finally isolated by flash chromatography.
📌 参考资料/链接：
参考文献标题:Inhibition of fatty acid synthase as a means to reduce adipocyte mass
文献作者:Kuhajda,F.P.; Mani,N.S.; Pasternack,G.R.; Townsend,C.A.(Johns Hopkins University)
参考来源:WO 9718806
📄 详细内容
合成路线:p-Methoxybenzyl itaconate (III) was prepared by reaction of itaconic anhydride (I) with p-methoxybenzyl alcohol (II) at 55-60 C (1).Condensation of the lithium enolate of (III) with nonanal (IV) in THF at -78 C gave adduct (V),which upon treatment with trifluoroacetic acid underwent cyclization and benzyl ester deprotection to yield the corresponding butyrolactone as a diastereomeric mixture.The major trans isomer was finally isolated by flash chromatography.
参考文献标题:Syntesis and antitumor activity of an inhibitor fatty acid synthase
文献作者:Kuhajda,F.P.; Pizer,E.S.; Li,J.N.; Mani,N.S.; Frehywot,G.; Townsend,G.A.
参考来源:Proceedings of the National Academy of Sciences of the United States of America 2000,97(7),3450
产品链接: CAS No. 191282-49-2›› 产品链接: CAS No.191282-48-1››