Syntheses of Puromycin from Adenosine and 7-Deazapuromycin from Tubercidin, and Biological Comparisons of the 7-Aza/Deaza Pair1

MJ Robins, RW Miles, MC Samano…

Index: Robins, Morris J.; Miles, Robert W.; Samano, Mirna C.; Kaspar, Roger L. Journal of Organic Chemistry, 2001 ,  vol. 66,  # 24  p. 8204 - 8210

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Citation Number: 28

Abstract

Protection (O5') of 2', 3'-anhydroadenosine with tert-butyldiphenylsilyl chloride and epoxide opening with dimethylboron bromide gave the 3'-bromo-3'-deoxy xylo isomer which was treated with benzylisocyanate 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- ...