Quantitation in the regioselectivity of acylation of glycosyl diglycerides: total synthesis of a Streptococcus pneumoniae α-glucosyl diglyceride

MB Richardson; DGM Smith; SJ Williams

Journal article

Quantitation in the regioselectivity of acylation of glycosyl diglycerides: total synthesis of a Streptococcus pneumoniae α-glucosyl diglyceride

MB Richardson, DGM Smith, SJ Williams

Chemical Communications | ROYAL SOC CHEMISTRY | Published : 2017

DOI: 10.1039/c6cc09584d

Abstract

The fidelity of acylation regioselectivity in the synthesis of mixed glycosyl diacylglycerols can be accurately measured by quantitative 13C 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.

University of Melbourne Researchers

Spencer Williams Author

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Grants

Awarded by Australian Research Council

Funding Acknowledgements

We thank the Australian Research Council (FT130100103, DP130102763, DP160100597) for financial support. We thank Dr Hamish Grant for technical assistance.