title: O-N intramolecular alkoxycarbonyl migration of typical protective groups in hydroxyamino acids.
abstract: O-N Intramolecular alkoxycarbonyl (carbonate-carbamate) migration was found to occur as a common reaction of hydroxyamino acids under mild basic aqueous conditions with no formation of side products. Carbonate protective groups migrate to produce amino-protected carbamate derivatives of hydroxyamino acids with high efficiency and purity.
authors.affiliation: Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st COE Program, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto 607-8412, Japan.
authors.forename: Mariusz
authors.initials: M
authors.lastname: Skwarczynski
authors.forename: Youhei
authors.initials: Y
authors.lastname: Sohma
authors.forename: Mayo
authors.initials: M
authors.lastname: Noguchi
authors.forename: Tooru
authors.initials: T
authors.lastname: Kimura
authors.forename: Yoshio
authors.initials: Y
authors.lastname: Hayashi
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Kiso
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry*; D002254:Carbonates / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D002219:Carbamates; D002254:Carbonates