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. 2021 Jul 15;50(3):1221–1240. doi: 10.1093/nar/gkab544

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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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Scheme 1. — Synthesis and separation of chiral PS dinucleotides as building blocks for oligonucleotide synthesis. B = nucleobase, uracil (U), adenine (A), guanine (G); Pg = protecting group, benzoyl (Bz) for A, N-isobutyryl (i-Bu) for G; R₁, R₂ = F and/or OMe; DMTr = dimethoxytrityl; TBS = tert-butyldimethylsilyl; CE = β-cyanoethyl; * except dimer gsa (Sp); ** except dimer gsa (Rp) (i) (a) 5-ethylthio-1H-tetrazole (ETT), solvent, rt; (b) phenylacetyl disulfide (PADS), 2,6-lutidine, rt; (ii) Et₃N·3HF, THF, rt to 50°C; (iii) 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite, 5-ethylthio-1H-tetrazole (ETT), solvent, 0°C to rt. Synthesis of each unique stereo-defined dinucleotide according to this scheme is described in detail in Materials and Methods and in Supplementary Information: III^Rp* refers to a, whereas the III^Sp** refers to b of compounds 3, 9, 15, 21, 27, 33 and 39; IV^Rp* refers to a, whereas the IV^Sp** refers to b of compounds 4, 10, 16, 22, 28, 34, and 40; V^Rp* refers to a, whereas the V^Sp** refers to b compounds 5, 11, 17, 23, 29, 35 and 41.