A comprehensive approach to the synthesis of sulfate esters.
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.
Simpson
Levi S
LS
Department of Chemistry, Indiana University, Bloomington, Indiana 47405-4001, USA.
Widlanski
Theodore S
TS
D005947:Glucose / Q000031:analogs & derivatives; D013463:Sulfuric Acid Esters / Q000138:chemical synthesis* / Q000737:chemistry; D014443:Tyrosine / Q000031:analogs & derivatives / Q000737:chemistry
D013463:Sulfuric Acid Esters; C005662:tyrosine O-sulfate; D014443:Tyrosine; D005947:Glucose