Synthesis and Glycosylation of Various Ceramide Derivatives via Borinic Acid Catalysis

摘要

Glycosphingolipids (GSLs) have become of increased interest due to recent realization that they may place a role in neurological diseases and cancer. Chemical synthesis of GSLs from simple building blocks requires efficient, yet selective methods to develop the major two components: ceramide and the carbohydrate. Much effort has been done to develop synthesis of the individual components; however the construction of the O-glycosidic bond that connects them has been plagued with regio- and stereoselectivity issues. In the past, both the ceramide and carbohydrate had to be chemically modified for the glycosylation step to occur with good selectivity and yields, but recently unprotected ceramides have been used with protected donors. Borinic acid catalysis has been an important advance in this field, allowing for higher yields and excellent beta-selectivity to develop GSLs. This thesis describes the synthesis of various ceramide derivatives and their corresponding glycosylation by borinic acid catalysis.