title: Direct synthesis of methyl phosphoramidates in carbohydrates.
abstract: A direct installation of a methyl phosphoramidate group by using methyl benzylphosphoramidochloridate into carbohydrates and amino acid is described. This one-step synthesis is efficient for both primary and secondary alcohols and exhibited excellent regioselectivity and functional group compatibility. Formation of a single diastereomer is observed in certain cases. The N-benzyl protecting group on methyl phosphoramidates is easily removed under mild conditions.
authors.affiliation: Institute of Chemistry, Academia Sinica, 128, Section 2, Academia Road, Taipei 115, Taiwan. wangcc@chem.sinica.edu.tw.
authors.forename: Vijay M
authors.initials: VM
authors.lastname: Dhurandhare
authors.forename: Girija Prasad
authors.initials: GP
authors.lastname: Mishra
authors.forename: Sarah
authors.initials: S
authors.lastname: Lam
authors.forename: Cheng-Chung
authors.initials: CC
authors.lastname: Wang
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry*; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000577:Amides; D002241:Carbohydrates; D010756:Phosphoric Acids; C011067:phosphoramidic acid