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新产品编号:1906819

Chemical Name: N-[1(R)-(Hydroxymethyl)-2-oxo-2-(8-oxo-1-oxaspiro[2.5]octa-4,6-dien-5-ylamino)ethyl]decanamide
项目整合开发状态: Biological Testing
项目研究机构: Universit鋞 Karlsruhe (Originator)
合成路线:Coupling of decanoylchloride (I) with D-serine (II) under Schotten-Baumann conditions (with Na2CO3 in H2O/THF) provides N-decanoyl-D-serine (III).Separately,aldehyde (IV) is reduced by means of NaBH4 in EtOH to yield alcohol (V),whose nitro group is reduced by means of In and NH4Cl in EtOH to afford substituted aniline (VI).Coupling of 5-amino-2-hydroxybenzyl alcohol (VI) with serine (III) by means of dicyclohexylcarbodiimide (DCC) and 1-hydroxybenzotriazole (HOBt) in DMF furnishes compound (VII),which is finally oxidized with NaIO4 in MeOH/H2O to yield the desired spiroepoxide.
📌 参考资料/链接:
参考文献标题:Synthesis of the first selective irreversible inhibitor of neutral sphingomyelinase
文献作者:Giannis,A.; Arenz,C.
参考来源:Angew Chem.Int Ed Engl 2000,39(8),1440