Analogues of moranoline and MDL 73945. Methyl 6(5)-deoxy-6(5)-(morpholin-4-yl)-alpha-D-glycosides as glucosidase inhibitors

Methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-alpha-D-glucopyranoside (6) , or its iodo analogue 7, were subjected to nucleophilic displacement with morpholine to give 8, deacetylation of which gave methyl 6-deoxy-6-(morphol in-4-yl)-alpha-D-glucopyranoside (3). Similarly, 11, 12 and 21 were prepare d. The 6-deoxy-6-iodo derivative 16 was subjected to nucleophilic displacem ent with morpholine and subsequent acetylation to give 15. Deacetylation of 15 gave 17. The kinetic studies for the inhibition of beta-D-glucosidase f rom sweet almond and using o-nitrophenyl beta-D-glucopyranoside as substrat e exhibited a K-i value for 21 on the same order as 1-deoxynojirimycin wher eas for 3, a K-i value of lesser order was observed.