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Synthesis of Thioglycoside Analogues of Maradolipid

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posted on 19.04.2013, 00:00 by Xiaojun Zeng, Raymond Smith, Xiangming Zhu
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.