American Chemical Society
jo026627c_si_002.pdf (4.43 MB)

A Practical Route to 3‘-Amino-3‘-deoxyadenosine Derivatives and Puromycin Analogues

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journal contribution
posted on 2003-02-06, 00:00 authored by Nhat Quang Nguyen-Trung, Oliver Botta, Silvia Terenzi, Peter Strazewski
3‘-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.