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A Nanospherical Ordered Mesoporous Lewis Acid Polymer for the Direct Glycosylation of Unprotected and Unactivated Sugars in Water
Author(s) -
Zhang Fang,
Liang Chao,
Wu Xiaotao,
Li Hexing
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201404353
Subject(s) - catalysis , mesoporous material , xanthone , chemistry , lewis acids and bases , glycosylation , trifluoromethanesulfonate , monosaccharide , lewis acid catalysis , organic chemistry , yield (engineering) , silanol , combinatorial chemistry , materials science , biochemistry , metallurgy
The design of robust solid catalysts which can selectively synthesize highly functionalized carbohydrate derivatives from unprotected and unactivated simple sugars in water is an outstanding challenge. Herein we describe the preparation of a novel nanospherical ordered mesoporous Lewis acid polymer (Sc(OTf) 2 ‐NSMP) by functionalizing the mesoporous phenol‐formaldehyde polymer framework with scandium triflate groups. In the C‐glycosylation reaction between D ‐glucose and dimedone with the Sc(OTf) 2 ‐NSMP catalyst, the conversion was 99 % and the yield of xanthone‐ C ‐glucoside reached 92 % after 2 days, which exceeded the previous best results. It was shown that other xanthone glycosides can be obtained from various sugars with moderate to good yields. Furthermore, the catalyst can be easily recovered and reused at least seven times without loss of catalytic activity.