Protecting of a thermolabile protecting group: "click-clack" approach.
A new method for attaining higher stability of thermolabile protecting groups (TPG) using an intramolecular cyclization through a "click-clack" approach was demonstrated. It was found that during intramolecular cyclization of 2-pyridyl type of TPG the thermally stable 3-pyridyl-[1,3,2]oxazaphospholidine ring was formed and thermolabile properties were declined. Thermolability could be recovered upon hydrolytic ring-opening of a 3-pyridyl-[1,3,2]oxazaphospholidine. "Click-clack" chemistry was applied to the synthesis of biologically important phosphate esters and their analogues and some H-phosphonate derivatives.
Chmielewski
Marcin K
MK
Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-704 Poznań, Poland. maro@ibch.poznan.pl
D002625:Chemistry, Organic / Q000379:methods; D003500:Cyclization; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010080:Oxazoles / Q000737:chemistry*
D009943:Organophosphorus Compounds; D010080:Oxazoles