Improved anomeric selectivity for the aroylation of sugars
M Teresa Barros1, Christopher D Maycock, Paula Rodrigues
1Departamento de Quimica, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, P-2825-114 Caparica, Portugal.
Abstract:
By manipulating the solvent and using bulky TMEDA as a base, good yields and improved anomeric selectivities were obtained for the aroylation of D-glucose over similar esterifications using pyridine. The reaction has been extended to mannose and the beta-anomer of pergalloylated mannose was predominantly obtained in one step by direct aroylation of the parent sugar.
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