Phosphorylation of several
D-glucose derivatives has been achieved using inorganic monoimido-
cyclo-triphosphate (MCTP, Na
3P
3O
8NH) in aqueous solution. In the phosphorylation of
D-glucose,
D-glucuronic acid, 2-deoxy-
D-glucose and
D-galactose, 1-
O-diphosphoramidophosphono-β-
D-glucose, 1-
O-diphosphoramidophosphono-β-
D-glucuronic acid, 1-
O-diphosphoramidophosphono-2-deoxy-β-
D-glucose, and 1-
O-diphosphoramidophosphono-β-
D-galactose were stereoselectively synthesized with yields of 54, 32, 37 and 46%, respectively. In the case of methyl α-
D-glucoside, the phosphorylated products were methyl 3-
O-diphosphoramidophosphono-α-
D-glucoside and methyl 4-
O-diphosphoramidophosphono-α-
D-glucoside, and in the case of methyl β-
D-glucoside the products were methyl 2-
O-diphosphoramidophosphono-β-
D-glucoside, methyl 3-
O-diphosphoramidophosphono-β-
D-glucoside, and methyl 4-
O-diphosphoramidophosphono-β-
D-glucoside. For
D-mannose and
D-allose, several phosphorylated products were obtained and the main products were 1-
O-diphosphoramidophosphono-β-
D-aldoses.
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