Simple syntheses of 4-O-glucosylated 1-deoxynojirimycins from maltose and cellobiose.
Glucosidase inhibitors alpha-D-glucopyranosyl-(1-->4)-1-deoxynojirimycin and beta-D-glucopyranosyl-(1-->4)-1-deoxynojirimycin were prepared from maltose and cellobiose, respectively, via the corresponding 5,6-eno derivatives, their epoxidation and the subsequent double reductive amination of the resulting 5-uloses. In both cases, the reported route is the first chemical synthesis not based on enzymatic glucosyl transfer.
Steiner
Andreas J
AJ
Glycogroup, Institut für Organische Chemie der Technischen Universität Graz, Stremayrgasse 16, A-8010 Graz, Austria.
Stütz
Arnold E
AE
D002475:Cellobiose / Q000737:chemistry; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D005947:Glucose / Q000737:chemistry; D065089:Glycoside Hydrolase Inhibitors; D006031:Glycosylation; D008320:Maltose / Q000737:chemistry
C478924:1-deoxy-nojirimycin; D065089:Glycoside Hydrolase Inhibitors; D002475:Cellobiose; D008320:Maltose; D005947:Glucose; D005944:Glucosamine