PDF herunterladen
Synthesis 2019; 51(15): 2984-3000
DOI: 10.1055/s-0037-1611801
paper
© Georg Thieme Verlag Stuttgart · New York

An Unexpected FeCl3/C-Catalyzed β-Stereoselective Glycosylation in the Presence of the C(2)-Benzyl Group

Hong Guo
a   School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200241, P. R. of China   eMail: Jbzhang@chem.ecnu.edu.cn
,
Wenshuai Si
a   School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200241, P. R. of China   eMail: Jbzhang@chem.ecnu.edu.cn
,
Juan Li
a   School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200241, P. R. of China   eMail: Jbzhang@chem.ecnu.edu.cn
,
Guofang Yang
a   School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200241, P. R. of China   eMail: Jbzhang@chem.ecnu.edu.cn
,
Tianjun Tang
a   School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200241, P. R. of China   eMail: Jbzhang@chem.ecnu.edu.cn
,
Zhongfu Wang
b   School of Life Sciences, Northwest University, Xi’an, 710069, P. R. of China
,
Jie Tang
a   School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200241, P. R. of China   eMail: Jbzhang@chem.ecnu.edu.cn
,
Jianbo Zhang  *
a   School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200241, P. R. of China   eMail: Jbzhang@chem.ecnu.edu.cn
› InstitutsangabenThe project was financially supported by Natural Science Foundation of Shanghai (11ZR1410400) and Open Foundation of East China Normal University (20151043 & 20162015).
Weitere Informationen

Publikationsverlauf

Received: 11. November 2018

Accepted after revision: 25. März 2019

Publikationsdatum:
26. April 2019 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik


Abstract

An efficient and completely β-stereoselective glycosylation that did not rely on neighboring group participation is described using 2–20 mol% FeCl3/C as the catalyst and benzylated propargyl glycosides as the donors to reach yields up to 96% under mild condition. With an octatomic-ring intermediate at the α-face of FeCl3/C with alkyne of propargyl glycosides, a panel of aglycones comprising aliphatic, alicyclic, unsaturated alcohols, halogenated alcohols, and phenols with different substitution were examined successfully for the exclusive β-stereoselective glycosylation reaction.

Key words

propargyl glycosides - glycosylation - β-stereoselective - C(2)-benzyl group - FeCl3/C

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611801.
  • Supporting Information