Convenient synthesis of the immunogenic glycolipid BbGL1

JÄGER, SEBASTIÁN N.; PORTA, EXEQUIEL O.J.; LABADIE, GUILLERMO R.

STEROIDS

ELSEVIER SCIENCE INC

Año: 2019 vol. 141 p. 41 - 45

0039-128X

A simple and efficient method to synthesize the immunogenic glycolipid BbGL1 is introduced. Two simple steps were required to obtain the desired product in good yield. First, a highly efficient glycosylation of cholesterol using galactosyl trichloroacetimidate as a donor was performed to produce cholesteryl-β-D-galactoside. Finally, an efficient palmitoylation on the C6?OH of the galactose of the synthesized saponin using sym-collidine and acyl chloride under microwave heating that produced BbGL1 in good yield. The procedure is a convenient and cheaper alternative to the reported procedures allowing a rapid preparation of multiple analogs and conjugates.