title: A comprehensive approach to the synthesis of sulfate esters.
abstract: A comprehensive approach to the synthesis of sulfate esters was developed. This approach permits the direct and high-yielding synthesis of protected sulfate monoesters. Subsequent deblocking to reveal sulfate monoesters is accomplished in near-quantitative yield. The exceptionally stable neopentyl protecting group and the labile isobutyl protecting group were utilized in the synthesis of aromatic and aliphatic sulfate monoesters. Strategies for tuning protecting group reactivity were also explored and developed.
authors.affiliation: Department of Chemistry, Indiana University, Bloomington, Indiana 47405-4001, USA.
authors.forename: Levi S
authors.initials: LS
authors.lastname: Simpson
authors.forename: Theodore S
authors.initials: TS
authors.lastname: Widlanski
mesh_terms: D005947:Glucose / Q000031:analogs & derivatives; D013463:Sulfuric Acid Esters / Q000138:chemical synthesis* / Q000737:chemistry; D014443:Tyrosine / Q000031:analogs & derivatives / Q000737:chemistry
chemical_list: D013463:Sulfuric Acid Esters; C005662:tyrosine O-sulfate; D014443:Tyrosine; D005947:Glucose