| Abstract
| - Protection (O5‘) of 2‘,3‘-anhydroadenosine with tert-butyldiphenylsilyl chloride and epoxide openingwith dimethylboron bromide gave the 3‘-bromo-3‘-deoxy xylo isomer which was treated withbenzylisocyanate to give the 2‘-O-(N-benzylcarbamoyl) derivative. Ring closure gave the oxazolidinone, and successive deprotection concluded an efficient route to 3‘-amino-3‘-deoxyadenosine.Analogous treatment of the antibiotic tubercidin {7-deazaadenosine; 4-amino-7-(β-d-ribofuranosyl)pyrrolo[2,3-d]pyrimidine} gave 3‘-amino-3‘-deoxytubercidin. Trifluoroacetylation of the 3‘-aminofunction, elaboration of the heterocyclic amino group into a (1,2,4-triazol-4-yl) ring with N,N‘-bis[(dimethylamino)methylene]hydrazine, and nucleophilic aromatic substitution with dimethylaminegave puromycin aminonucleoside [9-(3-amino-3-deoxy-β-d-ribofuranosyl)-6-(dimethylamino)purine]and its 7-deaza analogue. Aminoacylation [BOC-(4-methoxy-l-phenylalanine)] and deprotection gavepuromycin and 7-deazapuromycin. Most reactions gave high yields at or below ambient temperature.Equivalent inhibition of protein biosynthesis in a rabbit reticulocyte system and parallel growthinhibition of several bacteria were observed with the 7-aza/deaza pair. Replacement of N7 in thepurine ring of puromycin by “CH” has no apparent effect on biological activity.
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