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- W2143172905 abstract "In this paper we present revised and significantly improved synthetic routes to 2'-amino-LNA (locked nucleic acid). The optimal route is convergent with the synthesis of LNA monomers (2'-oxy-LNA) via a common intermediate obtained by a mild deacetylation for the liberation of the 2'-hydroxy group to give compound 23 without the concomitant ring closure that affords the 2'-oxy-LNA skeleton. After inversion of the stereochemistry at C2' and triflate formation at the 2'-hydroxy group a new common intermediate 16 is obtained which gives easy access to a range of other analogues exemplified by the introduction of a sulfur nucleophile leading to the 2'-thio-LNA structure. After substitution of the triflate with azide a basic reduction affords the desired 2'-amino-LNA structure, i.e., compound 18. This new synthesis strategy towards 2'-amino-LNA improves the overall yield significantly and converges the syntheses of 2'-oxy-LNA and LNA analogues." @default.
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- W2143172905 date "2003-01-21" @default.
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- W2143172905 title "Synthesis of 2′-amino-LNA: a new strategyElectronic supplementary information (ESI) available: further experimental details and the structure of compound S11 (.pdb file). See http://www.rsc.org/suppdata/ob/b2/b208864a/" @default.
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- W2143172905 doi "https://doi.org/10.1039/b208864a" @default.
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