A general synthesis of iminosugars.
1-Deoxynojirimycin, 1-deoxymannojirimycin, and 1-deoxygalactostatin have been synthesized by epoxidation of tri-O-acetyl-6-deoxyhex-5-enopyranosyl azides followed by methanolysis, deacetylation, and catalytic hydrogenation. 1,6-Dideoxygalactostatin was obtained by the reaction of 2,3,4-tri-O-acetyl-6-deoxy-beta-L-arabino-hex-5-enopyranosyl azide with NIS in methanol followed by deacetylation and catalytic hydrogenation. The overall yields were 4.4-23.5% over seven to nine steps.
McDonnell
Ciaran
C
Centre for Synthesis and Chemical Biology, Chemistry Department, Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland.
Cronin
Linda
L
O'Brien
Julie L
JL
Murphy
Paul V
PV
D017485:1-Deoxynojirimycin / Q000138:chemical synthesis; D019380:Anti-HIV Agents / Q000737:chemistry; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000138:chemical synthesis*; D005688:Galactosamine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D007097:Imines / Q000138:chemical synthesis*
D019380:Anti-HIV Agents; D002241:Carbohydrates; D007097:Imines; D017485:1-Deoxynojirimycin; D005688:Galactosamine