Synthesis of chiral pyrrolidine and piperidine glycosidase...

Details Synthesis of chiral pyrrolidine and piperidine glycosidase... Synthesis of chiral pyrrolidine and piperidine glycosidase...

C - Chemistry, Metallurgy

07

D

260/323, 260/292

C07D 207/12 (2006.01) C07D 207/16 (2006.01) C07D 211/46 (2006.01) C07D 211/60 (2006.01)

Patent

CA 2034643

07-27(660)A SYNTHESIS OF CHIRAL PYRROLIDINE AND PIPERIDINE GLYCOSIDASE INHIBITORS Abstract of the Disclosure There is disclosed a novel method for the syntheses of chiral pyrrolidines and piperidines by the intramolecular ring closure of anomeric mixtures of 4-amino- and 5-amino-2-trifluoromethanesulfonates of methyl furanosides. The novel method preferably provides for the efficient syntheses from diacetone glucose of 1,4-dideoxy-1,4-imino-D- arabinitol - known as DAB1, (2S,3R,4R)-3,4- dihydroxyproline, fagomine [1,5-imino-1,2,5- trideoxy-D-arabino-hexitol], and (2S,3R,4R)- 3,4-dihydroxypipecolic acid by intramolecular nucleophilic displacement by an amino function of 2-O-trifluoromethanesulphonates of anomeric mixtures of methyl furanosides.

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