Abstract
Recent studies have shown that the lipid antigens by the immune system is important for antiviral and antitumer. The aim of this study is synthesis of amino-ceramide as a core compound that coupling with various acids for constructing library of screenning experiment via amide bond formation. As the starting material is serin. Amino group of serin was first protected with Boc2O, followed by methylation and acetonidation to forming N,O-isopropylidine. Then reduced ester group into hydroxyl group. The main skeleton structure was constructed by Swern oxidation of selective oxidation to Garner’s aldehyde. Design different length sphingosine-based with Wittig Reaction, and utilized acylation to coupling via amide-bond formation, then synthesis of building block "ceramide acceptor" of glycolipid. While function group converted to amine compound (OH → NH2), then regard Tf2O as leaving group. As the hydrogen atom of amide bond would effect reaction, that lead to cyclolization phenomenon of elimination. It was unable to expect to get the amino-ceramide analog as target compound, that conjecture aboue mechanism with another pathway and discuss it. Due to lipid analogs its high hydrophobic, and the change of lipid antigen structure may cause the increase and decrease of the antigen activation. In future, it provide bioassay studies to expect to find out the potential compound with high efficiency screening.