This invention discloses a method for preparing lanamivir I. The method includes: starting with N-acetylneuraminic acid, esterification to obtain II, followed by
acetylation and cyclization without separation to obtain III; then deacetylation to obtain IV, followed by
carbonate esterification to obtain V; etherification to obtain VI, followed by
azide ring-opening to obtain VII;
azide reduction to obtain VIII, followed by guanidinolation to obtain IX; then
ester hydrolysis to obtain X; and finally deprotection of the Boc
protecting group to obtain lanamivir I, with an overall yield of 25-46%. This invention uses
thionyl chloride to catalyze methyl esterification, ensuring complete reaction without separation and allowing direct use in the next step; it utilizes
trimethylsilyl trifluoromethanesulfonate as a catalyst to achieve a one-step
acetylation and cyclization reaction, simplifying the operation; the
azide ring-opening
reaction conditions are mild, requiring no strict
temperature control, and the yield can reach 88.9%; simultaneously, a
crystallization purification step is introduced after guanidinolation, making the intermediate quality controllable, and the final product yield can reach over 85%.