Journal of Carbohydrate Chemistry p. 345 - 357 (2000)
Update date:2022-08-10
Topics:
El Ashry, El Sayed H.
Abdel-Rahman, Adel A.-H.
Kattab, Mohamed
Shobier, Aida H.
Schmidt, Richard R.
Methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-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-(morpholin-4-yl)-α-D-glucopyranoside (3). Similarly, 11, 12 and 21 were prepared. The 6-deoxy-6-iodo derivative 16 was subjected to nucleophilic displacement with morpholine and subsequent acetylation to give 15. Deacetylation of 15 gave 17. The kinetic studies for the inhibition of β-D-glucosidase from sweet almond and using o-nitrophenyl β-D-glucopyranoside as substrate exhibited a Ki value for 21 on the same order as 1-deoxynojirimycin whereas for 3, a Ki value of lesser order was observed.
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