Nhat Quang Nguyen-Trung, Oliver Botta, Silvia Terenzi and Peter Strazewski*
Journal of Organic Chemistry 2003, 68, 2038-2041.

A practical route to 3'-amino-3'-deoxyadenosine derivatives and puromycin analogs  
3'-Aminoacylamino-3'-deoxyadenosines, analogs 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 analogs were obtained in ten steps and up to 23% (14c) overall yield.