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- ...

2627-64-7

2′,3′-Anhydroad...

~97%

Synthesis of 3′-azido-and 3′-amino-3′-deoxyadenosine in both...

[Botta, Oliver; Moyroud, Elisabeth; Lobato, Cinta; Strazewski, Peter Tetrahedron, 1998 , vol. 54, # 44 p. 13529 - 13546]

An efficient synthesis of 3′??amino??3′??deoxyguanosine from...

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From adenosine to 3'-deoxyadenosine: development and scale u...

[Schirmeister-Tichy, Helga; Iacono, Kathryn T.; Muto, Nicholas F.; Homan, Joseph W.; Suhadolnik, Robert J.; Pfleiderer, Wolfgang Helvetica Chimica Acta, 1999 , vol. 82, # 4 p. 597 - 613]