High yield selective acylation of polyamines: proton as protecting group.
An advance in the selective acylation of polyamines having identical or similar amine functions is reported. While nucleophilicity differences between the various amine functions are slight, the corresponding conjugate acids exhibit pKa values over a significant range. We have used proton as polyamine protecting group: the monoamine resulting from single deprotonation of a polyammonium compound has allowed for high yields of selective acylation.
Oganesyan
Asmik
A
Department of Chemistry & Biochemistry, California State University, Los Angeles, California 90032-8202, USA.
Cruz
Iris A
IA
Amador
Roberto B
RB
Sorto
Nohemy A
NA
Lozano
Jose
J
Godinez
Carlos E
CE
Anguiano
Jaime
J
Pace
Heather
H
Sabih
Ghiwa
G
Gutierrez
Carlos G
CG
D000215:Acylation; D008968:Molecular Conformation; D011073:Polyamines / Q000138:chemical synthesis* / Q000737:chemistry; D011522:Protons; D000644:Quaternary Ammonium Compounds / Q000737:chemistry; D013237:Stereoisomerism
D011073:Polyamines; D011522:Protons; D000644:Quaternary Ammonium Compounds