title: Synthesis of the glycosphingolipid beta-galactosyl ceramide and analogues via olefin cross metathesis.
abstract: The preparation of the glycosphingolipid galactosyl ceramide from an orthogonally protected five-carbon building block is described. The main chain of the lipid is installed via a highly stereoselective olefin cross metathesis reaction. The methodology permits the facile preparation of glycolipids which vary in the length of the main carbon chain.
authors.affiliation: Department of Chemistry, Brown University, Box H, Providence, Rhode Island 02912, USA.
authors.forename: Anand Narain
authors.initials: AN
authors.lastname: Rai
authors.forename: Amit
authors.initials: A
authors.lastname: Basu
mesh_terms: D002518:Ceramides / Q000138:chemical synthesis* / Q000737:chemistry*; D005690:Galactose; D006026:Glycoside Hydrolases / Q000138:chemical synthesis* / Q000737:chemistry; D006028:Glycosphingolipids / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D002518:Ceramides; D006028:Glycosphingolipids; D007202:Indicators and Reagents; D006026:Glycoside Hydrolases; C023112:exo-beta-D-galactofuranosidase; D005690:Galactose