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Investigation of Glycosyl Nitrates as Building Blocks for Chemical Glycosylation
Author(s) -
Wang Tinghua,
Singh Yashapal,
Stine Keith J.,
Demchenko Alexei V.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801272
Subject(s) - chemistry , glycosylation , glycosyl , combinatorial chemistry , organic chemistry , stereochemistry , biochemistry
Glycosyl nitrates are important synthetic intermediates in the synthesis of 2‐amino sugars, 1,2‐orthoesters or, more recently, 2‐OH glucose. However, glycosyl nitrates have never been glycosidated. Presented herein is our first attempt to use glycosyl nitrates as glycosyl donors for O ‐glycosylation. Lanthanide triflates showed good affinity to activate the nitrate leaving group.