Synthesis of a quaternary polyprenyl ammonium salt.
Reaction of primary C(55)-allylic alcohol moraprenol (WT(3)C(7-9)-OH, a polyprenol from mulberry leaves) with triethylamine in the presence of phosphorus oxychloride leads to a quaternary ammonium chloride with a good yield (72%) and high cis-stereoselectivity of the terminal isoprene unit. Cationic polyprenyl derivatives may be useful for transfection and immunological studies.
Sizova
Olga V
OV
Kochetkov Laboratory of Carbohydrate Chemistry, Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation. olga_sizova@yahoo.co.uk
Utkina
Natalia S
NS
Kalinchuk
Nadezhda A
NA
Danilov
Leonid L
LL
Maltsev
Sergey D
SD
D009682:Magnetic Resonance Spectroscopy; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000644:Quaternary Ammonium Compounds