Synthesis Of Neuraminidase Inhibitors Laninamivir Octanoate

Laninamivir octanate is a long-acting selective neuraminidase inhibitors[4], Itstrade name: INAVIR, Chemical name:compoundⅠ:(2R,3R,4S)-3-acetamido-4-guanidino-2-[(1R,2R)-2-hydroxy-compound-1-methoxy-3-(octanoyl oxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylic acid; compoundⅡ(2R,3R,4S)-3-acetamido-4-guanidino-3-[(1R,2R)-2-hydroxy-1-methoxy-2-(octanoyl oxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylic acid, In this paper laninamivirioctanoate and related intermediates preparation was studied, Provides someintermediate nuclear magnetic data and the Target compounds of IR, MS and HPLCdata.In this paper we ues the N-acetylneuraminic acid as raw material, through a9-step chemical reaction and get the target product Laninamivir octanoate,1) in thepreparation of compound6, we select trimethylsilyl azide instead of sodium azide atroom temperature for introducing azido, avoiding the explosion of sodium azide atelevated temperatures;2)in the synthesis of compound7we use triphenylphosphine(Staudinger reaction) instead of hydrogen and Lindlar catalyst reduction reaction,greatly shorten the reaction time, the reaction at the same time without any treatmentcan be put down step reaction, is a step one-pot reaction;3)In the9-hydroxy avoid theuse of the original bitterness chain trimethyl (currently still can not buy the originalacid trimethyl new and own synthesis also requires a high cost) we use Octanoylchloride and9hydroxy ester into;4) After9steps the final product was synthesized,the target compound Purification by Recrystallization to give the pure product.