A novel O-fucosylation strategy preactivated by (p-Tol)2SO/Tf2O and its application for the synthesis of Lewis blood group antigen Lewisa. Issue 22 (31st May 2017)

• Record Type: Journal Article
• Authors: Li, Cui-yun; Liu, Guang-jian; Du, Wei; Zhang, Yuan; Xing, Guo-wen
• Is Part Of: Tetrahedron letters. Volume 58:Issue 22(2017)
• Page Start: 2109
• Page End: 2112
• Publication Date: 2017-05-31
• Subjects: Fucosylation -- Glycosylation -- Preactivation -- Lewisa synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.04.056
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A new O -fucosylation method promoted by ( p -Tol)2 SO/Tf2 O was reported. Secondary sugar alcohol acceptors gave high yields and α-stereoselectivities in the fucosylation. Lewis a was facilely synthesized in nine linear steps with 27% overall yield. Abstract: Based on a preactivation strategy using ( p -Tol)2 SO/Tf2 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.