Synthesis of mannojirimycin derivatives

Details Synthesis of mannojirimycin derivatives Synthesis of mannojirimycin derivatives

C - Chemistry, Metallurgy

07

D

260/276.2, 260/2

C07D 211/46 (2006.01) C07D 487/04 (2006.01) C07D 491/22 (2006.01) C07F 7/08 (2006.01) C07F 7/18 (2006.01)

Patent

CA 2024843

.alpha.-Homojirimycin and 6-dpi-homojirimycin are each synthesized from 2-azido-2-deoxy-3,4:6,7-di-O- isopropylidene-D-glycero-D-talo-heptono-1,5-lactone in which the side chain acetonide is hydrolyzed to give the corresponding diol which is then protected with a silyl protecting agent to form a silyl ether. The latter compound is used as a divergent intermediate in which the piperidine ring is formed by joining the nitrogen function at C-2 to C-6 (A) with inversion of configuration at C-6 to form 6- epi-homomannojirimycin or (B) with retention of configuration at C-6 to form .alpha.-homomannojirimycin.

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