jo026627c_si_002.pdf (4.43 MB)
A Practical Route to 3‘-Amino-3‘-deoxyadenosine Derivatives and Puromycin Analogues
journal contribution
posted on 2003-02-06, 00:00 authored by Nhat Quang Nguyen-Trung, Oliver Botta, Silvia Terenzi, Peter Strazewski3‘-Aminoacylamino-3‘-deoxyadenosines, analogues of the antibiotic puromycin, have been synthesized
from adenosine. They key 3‘-azido derivative 10 was obtained through a 3‘-oxidation/reduction/substitution procedure. A modified purification protocol on a larger scale was
developed for the oxidation step using the Garegg reagent.
The coupling reaction between an Fmoc-l-amino acid and
the fully protected form of 3‘-amino-3‘-deoxyadenosine 11
furnished the aminoacylated compounds 12 in high yields.
The puromycin analogues were obtained in 10 steps and up
to 23% (14c) overall yield.