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Synthesis of β ‐Mannosides via Prearranged Glycosides
Author(s) -
Ziegler Thomas,
Lemanski Gregor
Publication year - 1998
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/(sici)1521-3773(19981204)37:22<3129::aid-anie3129>3.0.co;2-8
Subject(s) - chemistry , disaccharide , glycoside , anomer , glycosylation , stereochemistry , intramolecular force , organic chemistry , biochemistry
The choice of activator is decisive for whether the α ‐(1→4)‐linked disaccharide 2 α or the anomeric compound 2 β is formed from the prearranged glycoside 1 . Other β ‐mannosylsaccharides can also be synthesized selectively by intramolecular glycosylation. Bn=benzyl, Bz=benzoyl, MeOTf= methyl trifluoromethanesulfonate, NIS= N ‐iodosuccinimide.