Improved anomeric selectivity for the aroylation of sugars.
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.
Teresa Barros
M
M
Departamento de Quimica, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, P-2825-114 Caparica, Portugal.
Maycock
Christopher D
CD
Rodrigues
Paula
P
Thomassigny
Christine
C
D005947:Glucose / Q000737:chemistry*; D008358:Mannose / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
D009942:Organometallic Compounds; D011725:Pyridines; D012997:Solvents; C450681:phenyllithium; D005947:Glucose; C023666:pyridine; D008358:Mannose