{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"omics_type":["Unknown"],"volume":["7(26)"],"submitter":["Herrera-Gonzalez I"],"pubmed_abstract":["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 sp<sup>2</sup>-iminosugar, whose preparation on a gram scale has been optimized, as the starting material. sp<sup>2</sup>-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 b"],"journal":["ACS omega"],"pagination":["22394-22405"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC9260894"],"repository":["biostudies-literature"],"pubmed_title":["Stereoselective 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."],"pmcid":["PMC9260894"],"pubmed_authors":["Garcia-Moreno MI","Ortiz Mellet C","Gonzalez-Cuesta M","Garcia Fernandez JM","Herrera-Gonzalez I"],"additional_accession":[]},"is_claimable":false,"name":"Stereoselective 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.","description":"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 sp<sup>2</sup>-iminosugar, whose preparation on a gram scale has been optimized, as the starting material. sp<sup>2</sup>-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 b","dates":{"release":"2022-01-01T00:00:00Z","publication":"2022 Jul","modification":"2025-04-04T21:40:53.093Z","creation":"2022-07-22T09:33:48.094Z"},"accession":"S-EPMC9260894","cross_references":{"pubmed":["35811898"],"doi":["10.1021/acsomega.2c01469"]}}