title: Synthesis of thioglycoside analogues of maradolipid.
abstract: 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.
authors.affiliation: College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, China.
authors.forename: Xiaojun
authors.initials: X
authors.lastname: Zeng
authors.forename: Raymond
authors.initials: R
authors.lastname: Smith
authors.forename: Xiangming
authors.initials: X
authors.lastname: Zhu
mesh_terms: D006017:Glycolipids / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D013237:Stereoisomerism; D013865:Thioglycosides / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D006017:Glycolipids; D013865:Thioglycosides; C568414:maradolipid