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. Author manuscript; available in PMC: 2014 May 5.
Published in final edited form as: Chemistry. 2013 Oct 14;19(47):15872–15878. doi: 10.1002/chem.201302188

Scheme 2.

Scheme 2

Synthesis of protected (S)-2-amino-4-(bis(allyloxy) phosphoryl) butanoic acid (All =allyl) and the 3′-amino-3′-deoxyadenosine-functionalized solid support. Reaction conditions: a) BuLi (2.5M in hexane, 1.0 equiv), compound 7 (0.9 equiv), diallyl(eth-2-enyl)phosphonate (elimination product of 7, 0.1 equiv), THF, −78°C to RT, 40 min, 85%. For details of chemical transformations of compound 8 to the solid support 10 and the synthesis of compounds 6 and 7 see the Supporting Information (SI).