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2000
Volume 15, Issue 2
  • ISSN: 1570-1786
  • E-ISSN: 1875-6255

Abstract

Background: Carbohydrate fatty acid esters are found in important biological molecules such as bile acid 1-O-acyl galacto and bacterial glycolipids. The synthesis of glycomimetics of those biomolecules is required to study their structure-activity relationship. Method: In this work a series of carbohydrate fatty acid esters were regioselectively prepared mainly via protection and deprotection and tin-mediated strategies of partially benzyl-protected sugars, followed by hydrogenolysis of the benzyl groups. Results: We report here the regioselective synthesis of galactose palmitoyl esters along with other fatty acyl galactose glycomimetics namely fucose and lactose fatty esters. 1-O-palmitoyl-, 1,6-di-Opalmitoyl- D-galactose and 1-O-palmitoyl-L-fucose derivatives were prepared via a low-temperature esterification of the partially benzyl-protected galactose and fucose derivatives, respectively, followed by hydrogenolysis of the benzyl groups. The regioselective synthesis of 3'-O-acyl-D-lactosides of palmitic and nitrobenzoic acids was accomplished using a dibutyltin oxide activation strategy of partially protected lactoside derivatives. Conclusion: The regioselective synthesis of galactose, fucose and lactose fatty acid esters as glycomimetics of biological molecules containing the 1-O-fatty acyl-D-galactose moiety is reported in this work.

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/content/journals/loc/10.2174/1570178614666170720141917
2018-02-01
2025-07-08
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