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Issue 70, 2012
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Efficient synthesis of 2′-C-α-aminomethyl-2′-deoxynucleosides§

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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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Publication details

The article was received on 25 Jun 2012, accepted on 12 Jul 2012 and first published on 12 Jul 2012


Article type: Communication
DOI: 10.1039/C2CC34556K
Chem. Commun., 2012,48, 8754-8756

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

    N. Li and J. A. Piccirilli, Chem. Commun., 2012, 48, 8754
    DOI: 10.1039/C2CC34556K

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