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. 2021 Nov 26;49(21):12089–12105. doi: 10.1093/nar/gkab1097

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© The Author(s) 2021. Published by Oxford University Press on behalf of Nucleic Acids Research.

This is an Open Access article distributed under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0/), which permits unrestricted reuse, distribution, and reproduction in any medium, provided the original work is properly cited.

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Figure 3. — Synthesis of purine building blocks. (a) N⁶-Benzoyladenine, BSA, TMSOTf, MeCN, 70°C, 20 min, 64%; (b) NaOH, THF/MeOH/H₂O, 0°C, 20 min, 51% α-anomer, 18% β-anomer; (c) Ac₂O, DMAP, DCM, rt, 18 h, 90%; (d) TBAF, THF, rt, 3.5 h, 90%; (e) DMTr-Cl, pyridine, rt, 24 h, 89%; (f) NaOH, THF/MeOH/H₂O, 0°C, 30 min, 94%; (g) 2-cyanoethyl N,N,N′,N′-tetraisopropylphosphordiamidite, ETT, DCM, rt, 1 h, 77% for 15, 50 min, 67% for 23; (h) 2-amino-6-chloropurine, BSA, TMSOTf, MeCN, 55°C, 50 min, 77%; (i) NaOH, THF/MeOH/H₂O, 0°C, 20 min, 85%; (j) TBD, 3-hydroxypropionitrile, DCM, 48 h, 87%; (k) Ac₂O, DMAP, DCM, rt, 48 h, 76%; (l) TBAF, THF, rt, 4 h, 87%; (m) DMTr-Cl, pyridine, rt, 48 h, 99%; (n) (i) K₂CO₃, MeOH, rt, 7 h, (ii) N,N-dimethylformamide dimethylacetal, DMF, 55°C, 2 h, 77%.