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β‐Mannosides from β‐Glucosides by Intramolecular Nucleophilic Substitution with Inversion of Configuration
Author(s) -
Kunz Horst,
Günther Wolfgang
Publication year - 1988
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198810861
Subject(s) - intramolecular force , substituent , chemistry , epimer , nucleophile , nucleophilic substitution , stereochemistry , medicinal chemistry , organic chemistry , catalysis
The β‐mannoside bond in the core region of N ‐glycoproteins is difficult to form. The epimerization at C‐2 of β‐glucosides, which is normally difficult to achieve, has now been accomplished by intramolecular nucleophilic attack of a carbamate substituent in the sense of neighboring‐group assistance. It was possible in this way to prepare directly isomerically pure (protected) β‐mannosides like 1 from menthol and cholesterol as well as β‐mannosidic disaccharides.