Synthesis of potential inhibitors of carbohydrate processing enzymes

The review article describes the synthesis of different C-glycoside mimetics of glycosylphosphates, glycolipids, glycosyl amino acids and oligosaccharides. In particular, the phosphono analogues of alpha-L-rhamnose 1-phosphate, N-acetyl-alpha-D-glucosamine and N-acetyl-alpha-D-mannosamine-1-phosphate were synthesised; the last two from a C-2-deprotected alpha-C-glucopyranoside, the free hydroxyl group of which was finally converted into an amino group. In this context a method for the deprotection of allyl C-glycosides at C-2 is also reported. Analogues of glycosyl glycerols were obtained by reaction of a malonyl radical with glycoexoenitols and reduction of the obtained beta-C-glycosyl malonate. Acylation gave the analogues of glyceroglycolipids. A C-glucosyl amino acid was obtained exploiting a Wittig rearrangement of compound 38. Naphthoquinone was attached, through C-C bonds, to the anomeric centre of a sugar and the non-reducing end of a different sugar, so affording a mimic of a trisaccharide. (C) 1998 Elsevier Science Ltd. All rights reserved.