Synthesis of Thioglycoside Analogues of Maradolipid

We
describe here the first synthesis of thioglycoside analogues
of maradolipid, based on a new procedure for the synthesis of 1-thiotrehalose
developed recently in our laboratories. The challenging α,α-(1→1′)
thioglycosidic linkage was constructed by Schmidt’s inverse
procedure in very high yield and excellent stereoselectivity. Subsequent
protecting group manipulation and coupling with different fatty acids
led smoothly to a group of symmetrical and unsymmetrical thiomaradolipids
which would be of high value for biological studies.