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. 2022 Jun 1;5:68. doi: 10.1038/s42004-022-00685-5

Fig. 8. Synthesis of 3′-thiophosphate-LNA-TTP 15 and 3′-β-cyano-thiophosphate-LNA-TTP 16.

Fig. 8

Reagents and conditions: (i) Beaucage reagent, pyridine, rt, 10 min, quantitative; (ii) TFA, DCM, rt, 60 min, quantitative; (iii) 2-chloro-1,3,2-benzodioxaphosphorin-4-one, pyridine, dioxane, rt, 45 min; 2. (nBu3NH)2 H2P2O7, DMF, nBu3N, rt, 45 min; 3. I2, pyridine, H2O, rt, 30 min; 4. NH4OH, MeNH2 (1:1), rt, 2 h, 5% over 4 steps; iv) 2-chloro-1,3,2-benzodioxaphosphorin-4-one, pyridine, dioxane, rt, 45 min; 2. (nBu3NH)2 H2P2O7, DMF, nBu3N, rt, 45 min; 3. I2, pyridine, H2O, rt, 30 min, 7% over 3 steps.