Novel synthesis of the glycosidase inhibitor deoxymannojirimycin and of a synthetic precursor D-lyxo-hexos-5-ulose.
[reaction: see text]. The synthesis of D-lyxo-hexos-5-ulose (5-ketomannose, 1,5-dicarbonyl sugar), a synthetic precursor to the glycoprocessing inhibitor deoxymannojirimycin, was carried out by an in situ epoxidation and hydrolysis of a trimethylsilyl-protected 6-deoxyhex-5-enopyranoside followed by facile removal of the protecting groups. A novel nine-step synthesis of deoxymannojirimycin has also been achieved from methyl alpha-D-mannopyranoside; this involved methanolysis of epoxides derived from an acetylated 1-azido-6-deoxyhex-5-enopyranoside followed by deprotection and catalytic hydrogenation.
O'Brien
J L
JL
Chemistry Department, Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland.
Tosin
M
M
Murphy
P V
PV
D017485:1-Deoxynojirimycin / Q000138:chemical synthesis*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D000998:Antiviral Agents / Q000138:chemical synthesis; D002626:Chemistry, Pharmaceutical; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D004852:Epoxy Compounds / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D008358:Mannose / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D008766:Methylmannosides / Q000737:chemistry
C448621:5-ketomannose; D000900:Anti-Bacterial Agents; D000998:Antiviral Agents; D004791:Enzyme Inhibitors; D004852:Epoxy Compounds; D008766:Methylmannosides; D017485:1-Deoxynojirimycin; C008466:methylmannoside; D006026:Glycoside Hydrolases; D008358:Mannose