The Journal of organic chemistry

Convenient syntheses of 3′-amino-2′, 3′-dideoxynucleosides, their 5′-monophosphates, and 3′-aminoterminal oligodeoxynucleotide primers

R Eisenhuth, C Richert

Index: Eisenhuth, Ralf; Richert, Clemens Journal of Organic Chemistry, 2009 , vol. 74, # 1 p. 26 - 37

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Citation Number: 25

Abstract

5′-Protected 3′-amino-2′, 3′-dideoxynucleosides containing any of the four canonical nucleobases (A/C/G/T) were prepared via azides in five to six steps, starting from deoxynucleosides. For pyrimidines, the synthetic route involved nucleophilic opening of anhydronucleosides. For purines, an in situ oxidation/reduction sequence, followed by a Mitsunobu reaction with diphenyl-2-pyridylphosphine and sodium azide, provided the 3′- ...