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A novel O -fucosylation strategy preactivated by ( p -Tol) 2 SO/Tf 2 O and its application for the synthesis of Lewis blood group antigen Lewis a

Authors :
Guang-jian Liu
Wei Du
Yuan Zhang
Guo-wen Xing
Cui-yun Li
Source :
Tetrahedron Letters. 58:2109-2112
Publication Year :
2017
Publisher :
Elsevier BV, 2017.

Abstract

Based on a preactivation strategy using ( p -Tol) 2 SO/Tf 2 O, a new O -fucosylation method with thioglycoside as donor under mild conditions was reported. High yields and excellent α-stereoselectivities of the fucosylation were obtained with secondary sugar alcohol as acceptors. Moreover, the novel fucosylation strategy was successfully applied to the synthesis of an important Lewis blood group antigen Lewis a , which was obtained in nine linear steps with 27% overall yield.

Details

ISSN :
00404039
Volume :
58
Database :
OpenAIRE
Journal :
Tetrahedron Letters
Accession number :
edsair.doi...........7f6abde8b8b5ac8da7baf3a952907a9e
Full Text :
https://doi.org/10.1016/j.tetlet.2017.04.056