Regioselective Synthesis of Novel Galactose, Fucose and Lactose Fatty Acid Esters as Glycomimetics of Bile Acid 1-O-acyl Galactoside and Bacterial Glycolipids

Author(s): Sahar A. Shehata, Mina R. Narouz, Sameh E. Soliman, Rafik W. Bassily, Ramadan I. El-Sokkary, Mina A. Nashed*.

Journal Name: Letters in Organic Chemistry

Volume 15 , Issue 2 , 2018

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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.

Keywords: Glycolipid, glycomimetics, sugar fatty acid esters, regioselective esterification, dibutyltin oxide, bile acid.

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Article Details

VOLUME: 15
ISSUE: 2
Year: 2018
Page: [147 - 154]
Pages: 8
DOI: 10.2174/1570178614666170720141917
Price: $65

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