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Stereoselective Synthesis of α‐ and β‐Glycofuranosyl Amides by Traceless Ligation of Glycofuranosyl Azides
Author(s) -
Nisic Filippo,
Speciale Gaetano,
Bernardi Anna
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201200309
Subject(s) - stereoselectivity , azide , chemistry , anomer , combinatorial chemistry , ligation , staudinger reaction , stereochemistry , organic chemistry , catalysis , microbiology and biotechnology , biology
Abstract A highly stereoselective synthesis of α‐ or β‐glycofuranosyl amides based on the traceless Staudinger ligation of glycofuranosyl azides of the galacto , ribo , and arabino series with 2‐diphenylphosphanyl‐phenyl esters has been developed. Both α‐ and β‐isomers can be obtained with excellent selectivity from a common, easily available precursor. The process does not depend on the anomeric configuration of the starting azide but appears to be controlled by the C2 configuration and by the protection/deprotection state of the substrates. A mechanistic interpretation of the results, supported by 31 P NMR experiments, is offered and merged with our previous mechanistic analysis of pyranosyl azide ligation reactions.