Synthesis of the glycosphingolipid beta-galactosyl ceramide and analogues via olefin cross metathesis.
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.
Rai
Anand Narain
AN
Department of Chemistry, Brown University, Box H, Providence, Rhode Island 02912, USA.
Basu
Amit
A
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
D002518:Ceramides; D006028:Glycosphingolipids; D007202:Indicators and Reagents; D006026:Glycoside Hydrolases; C023112:exo-beta-D-galactofuranosidase; D005690:Galactose