Open AccessA “Traceless” Directing Group Enables Catalytic SN2 Glycosylation toward 1,2-cis-Glycopyranosides
Author(s) -
Xu Ma,
Zhitong Zheng,
Yingjuan Fu,
Xijun Zhu,
Peng Liu,
Liming Zhang
Publication year - 2021
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.1c04584
Subject(s) - chemistry , glycosylation , glycosyl , anomer , sn2 reaction , stereoselectivity , catalysis , carbohydrate chemistry , oxazole , stereochemistry , group (periodic table) , combinatorial chemistry , leaving group , organic chemistry , biochemistry
Generally applicable and stereoselective formation of 1,2- cis -glycopyranosidic linkage remains a long sought after yet unmet goal in carbohydrate chemistry. This work advances a strategy to this challenge via stereoinversion at the anomeric position of 1,2- trans glycosyl ester donors. This S N 2 glycosylation is enabled under gold catalysis by an oxazole-based directing group optimally tethered to a leaving group and achieved under mild catalytic conditions, in mostly excellent yields, and with good to outstanding selectivities. The strategy is also applied to the synthesis of oligosaccharides.