10.1021/jo400274s.s002
Xiaojun Zeng
Xiaojun
Zeng
Raymond Smith
Raymond
Smith
Xiangming Zhu
Xiangming
Zhu
Synthesis of Thioglycoside Analogues of Maradolipid
American Chemical Society
2013
Subsequent
thioglycosidic
thiotrehalose
laboratory
Schmidt
procedure
Synthesi
group manipulation
unsymmetrical thiomaradolipids
MaradolipidWe
thioglycoside analogues
stereoselectivity
linkage
acid
Thioglycoside Analogues
synthesis
2013-04-19 00:00:00
Dataset
https://acs.figshare.com/articles/dataset/Synthesis_of_Thioglycoside_Analogues_of_Maradolipid/2422429
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.