title: Quantitation in the regioselectivity of acylation of glycosyl diglycerides: total synthesis of a Streptococcus pneumoniae α-glucosyl diglyceride.
abstract: The fidelity of acylation regioselectivity in the synthesis of mixed glycosyl diacylglycerols can be accurately measured by quantitative13C NMR spectroscopy using a 1-13C-labelled fatty acid and a paramagnetic relaxation enhancement agent. Exquisite regioselectivity is achieved using a stepwise acylation/substitution of a glycosyl β-bromohydrin, which is applied to the total synthesis of Streptococcus pneumoniae Glc-DAG-s2.
authors.affiliation: School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, Victoria 3010, Australia. sjwill@unimelb.edu.au.
authors.forename: Mark B
authors.initials: MB
authors.lastname: Richardson
authors.affiliation: School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, Victoria 3010, Australia. sjwill@unimelb.edu.au.
authors.forename: Dylan G M
authors.initials: DG
authors.lastname: Smith
authors.affiliation: School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, Victoria 3010, Australia. sjwill@unimelb.edu.au.
authors.forename: Spencer J
authors.identifier: http://orcid.org/0000-0001-6341-4364
authors.initials: SJ
authors.lastname: Williams