biostudies-literatureUnknown7(26)Herrera-Gonzalez IA simple and efficient method for the stereoselective synthesis of nojirimycin α-<i>C</i>-glycoside derivatives has been developed using a bicyclic carbamate-type sp²-iminosugar, whose preparation on a gram scale has been optimized, as the starting material. sp²-iminosugar <i>O</i>-glycosides or anomeric esters serve as excellent precursors of acyliminium cations, which can add nucleophiles, including <i>C</i>-nucleophiles. The stereochemical outcome of the reaction is governed by stereoelectronic effects, affording the target α-anomer with total stereoselectivity. Thus, the judicious combination of <i>C</i>-allylation, carbamate hydrolysis, cross-metathesis, and hydrogenation reactions provides a very convenient entry to iminosugar α-<i>C</i>-glycosides, which have bACS omega22394-22405https://www.ebi.ac.uk/biostudies/studies/S-EPMC9260894biostudies-literatureStereoselective Synthesis of Nojirimycin α-<i>C</i>-Glycosides from a Bicyclic Acyliminium Intermediate: A Convenient Entry to <i>N</i>,<i>C</i>-Biantennary Glycomimetics.PMC9260894Garcia-Moreno MIOrtiz Mellet CGonzalez-Cuesta MGarcia Fernandez JMHerrera-Gonzalez IfalseStereoselective Synthesis of Nojirimycin α-<i>C</i>-Glycosides from a Bicyclic Acyliminium Intermediate: A Convenient Entry to <i>N</i>,<i>C</i>-Biantennary Glycomimetics.A simple and efficient method for the stereoselective synthesis of nojirimycin α-<i>C</i>-glycoside derivatives has been developed using a bicyclic carbamate-type sp²-iminosugar, whose preparation on a gram scale has been optimized, as the starting material. sp²-iminosugar <i>O</i>-glycosides or anomeric esters serve as excellent precursors of acyliminium cations, which can add nucleophiles, including <i>C</i>-nucleophiles. The stereochemical outcome of the reaction is governed by stereoelectronic effects, affording the target α-anomer with total stereoselectivity. Thus, the judicious combination of <i>C</i>-allylation, carbamate hydrolysis, cross-metathesis, and hydrogenation reactions provides a very convenient entry to iminosugar α-<i>C</i>-glycosides, which have b2022-01-01T00:00:00Z2022 Jul2025-04-04T21:40:53.093Z2022-07-22T09:33:48.094ZS-EPMC92608943581189810.1021/acsomega.2c01469