Synthesis of carbohydrate methyl phosphoramidates.
A two-step route for introducing methyl phosphoramidate moieties onto carbohydrates is reported. The approach uses methyl pivolyl H-phosphonate as the phosphorylating reagent to produce an isolable carbohydrate H-phosphonate intermediate that is then oxidized by a Todd-Atherton reaction. The stability of the product methyl phosphoramidates was subsequently evaluated using various deprotection strategies.
Alberta Glycomics Centre and Department of Chemistry, The University of Alberta , Gunning-Lumieux Chemistry Centre, Edmonton, Alberta T6G 2G2, Canada.
Roger A
RA
Ashmus
Todd L
TL
Lowary
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010756:Phosphoric Acids / Q000138:chemical synthesis* / Q000737:chemistry; D010766:Phosphorylation
D000577:Amides; D002241:Carbohydrates; D010756:Phosphoric Acids; C011067:phosphoramidic acid