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. 2009 Jan 23;131(6):2119–2121. doi: 10.1021/ja809069b

Scheme 1. Synthesis of 2′-Amino Glycerol Nucleoside Monomers.

Scheme 1

For 1t−4t, B = thymine; for 1c−4c, B = N4-benzoylcytosine; for 1a−4a, B = N6-benzoyladenine; for 1g−4g, B = N2-isobutyrylguanine. For 3t, R1 = O, R2 = CH3; for 3c, R1 = NBz, R2 = H. Conditions and yields: (a) DAST, pyridine/CH2Cl2; 3t, not isolated; 3c, 54%. (b) NaN3, 1:1 DMF/HMPA, 110 °C; 4t, 42%; 4c, 46%. (c) (i) MesCl, Et3N/CH2Cl2 (ii) NaN3, 1:1 DMF/HMPA, 100 °C. 4a, 71%; 4g, 96%. (d) For 4t and 4g, H2, Pd/C, 78% and 77%, respectively; for 4c and 4a, H2S, 15% Et3N in Pyridine, 0 °C, 83% and 91%, respectively.