【药物名称】
化学结构式(Chemical Structure):
参考文献No.579041
标题:Synthesis of the first selective irreversible inhibitor of neutral sphingomyelinase
作者:Giannis, A.; Arenz, C.
来源:Angew Chem. Int Ed Engl 2000,39(8),1440
合成路线图解说明:

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.

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