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Beilstein J. Org. Chem. 2020, 16, 2854–2861, doi:10.3762/bjoc.16.234
Graphical Abstract
Scheme 1: Synthesis of a C8-linker-modified adenosine derivative. (a) 4 equiv TBDMS-Cl, 5 equiv imidazole, DM...
Figure 1: Characterization and assignment of the TBDMS isomers via HSQC (red) and HMBC (blue) NMR measurement...
Scheme 2: New synthetic route to the C8-linker modified adenosine building block. (a) i) 1.2 equiv di-tert-bu...
Beilstein J. Org. Chem. 2018, 14, 397–406, doi:10.3762/bjoc.14.28
Figure 1: Preparation of fully protected trinucleotides in solution (A), on solid phase (B) and on soluble po...
Figure 2: Strategies for trinucleotide synthesis using different pairs of orthogonal groups for protection of...
Figure 3: Strategy for the synthesis of nucleotide dimers and extension to the trimer in either 5'- or 3'-dir...
Figure 4: Removal of the 3'-O-protecting group under conditions that leave all other protecting groups at 5'-...
Figure 5: Release of trinucleotide blocks from the solid support by cleavage of an oxalyl anchor (A) and by a...
Figure 6: Release of the trinucleotide from the support under reductive conditions.
Figure 7: Phosphitylation of trimers. Reaction conditions, in particular the choice of the phosphitylation re...
Beilstein J. Org. Chem. 2014, 10, 1906–1913, doi:10.3762/bjoc.10.198
Figure 1: Retrosynthetic analysis of the bifunctional cytidine derivative 1 for functionalization of a period...
Figure 2: Introduction of the triazolyl moiety into the uridine derivative 7 generating synthon 3. I: 4 equiv...
Figure 3: Preparation of synthon 4 and substitution of the triazolyl moiety of 3 to form the fully protected ...
Figure 4: Synthesis of 2',3'-bis-O-(tert-butyldimethylsilyl)-1-[4-(N'-biotinyl-3,6-dioxaoctane-1,8-diamine)py...
Figure 5: Formation of the phosphoramidite 2 from amino alcohol 13, and subsequent coupling to the 5'-O-depro...
Figure 6: A) Reversed-phase HPLC purification of 1 after complete deprotection of 16. A represents the absorp...
Figure 7: Reaction scheme of periodate oxidation of a 20mer model RNA followed by coupling of cytidine deriva...
Figure 8: Reversed-phase HPLC analysis. A: Crude product of the coupling reaction between the 20mer model RNA...