Efficient synthesis of 2′-C-α-aminomethyl-2′-deoxynucleosides??§

Chemical Communications Pub Date: 2012-07-12 DOI: 10.1039/C2CC34556K

Abstract

Starting from methyl 3,5-di-O-benzyl-2-keto-α-D-ribofuranoside, a convergent, six-step synthesis is developed to give efficiently all four 2′-C-α-aminomethyl-2′-deoxynucleosides (U, C, A, G) in 38%, 42%, 12%, 12% yield, respectively. Convergence is achieved by the glycosylation of persilylated nucleobases with methyl 2-α-phthalimidomethyl ribofuranoside.

Graphical abstract: Efficient synthesis of 2′-C-α-aminomethyl-2′-deoxynucleosides
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