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Beilstein J. Org. Chem. 2017, 13, 806–816, doi:10.3762/bjoc.13.81
Graphical Abstract
Figure 1: Collidine-assisted vs DMAP-assisted N-methylation process on solid support. (A) Collidine-assisted ...
Figure 2: Motifs 1–5 were used as models for the optimization of the N-methylation process. i) Introduction o...
Figure 3: Sulfonylation optimization study. HPLC trace overlay that shows the sulfonylation of motif 4 to yie...
Figure 4: DFT calculations for the reaction of o-NBS-Cl with a) collidine and b) DMAP. The structure of the r...
Figure 5: Methylation of motif 3a to 3b using various reaction conditions. HPLC trace overlay presents the ef...
Figure 6: Optimization of o-NBS removal reaction conditions demonstrated on motif 5b. HPLC trace overlay of i...
Figure 7: HPLC trace overlay and MS analysis of the somatostatin analogue, 1SW-1, which was Nα-methylated on ...
Beilstein J. Org. Chem. 2016, 12, 1440–1446, doi:10.3762/bjoc.12.139
Figure 1: Disaccharide repeating unit of the S. pneumoniae serotype 3 CPS.
Figure 2: Building blocks and solid support for the automated solid-phase synthesis of S. pneumoniae serotype...
Scheme 1: Attempted assembly of SP3 trisaccharide 5 using glycosyl phosphate building blocks 1 and 2. Reagent...
Figure 3: HPLC chromatogram of the crude products of the attempted AGA of SP3 trisaccharide 5; conditions: YM...
Scheme 2: Attempted AGA of SP3 trisaccharide 9 using glycosyl phosphate building blocks 1 and 3. Reagents and...
Figure 4: HPLC chromatogram of the crude products of the attempted AGA of SP3 trisaccharide 9; conditions: YM...
Scheme 3: Automated synthesis of linker-bound glucuronic acid 10 using glycosyl phosphate building block 1. R...
Scheme 4: Automated synthesis of SP3 trisaccharide 5 using glycosyl phosphate building blocks 1 and 2. Reagen...
Figure 5: HPLC chromatogram of the crude products of the automated solid-phase SP3 trisaccharide 5 synthesis;...
Scheme 5: Global deprotection of SP3 trisaccharide 5. Reagents and conditions: a) LiOH, H2O2, THF, −5 °C to r...
Beilstein J. Org. Chem. 2012, 8, 1601–1609, doi:10.3762/bjoc.8.183
Figure 1: (a) Synthesis sequence for the preparation of building blocks 4 and 5; (b) Retrosynthetic analysis ...
Scheme 1: Reagents and conditions: (i) PhI(OAc)2, BF3·Et2O, CH2Cl2, −40 °C; then Ac2O, pyridine; (ii) N2H4·Ac...
Scheme 2: Reagents and conditions. (i) TMSOTf, DCM, −10 °C, 80%; (ii) NaOMe, MeOH; then KOH, MeOH, 60 °C; the...
Scheme 3: Automated synthesis of 20. Reagents and conditions: (i) (a) NIS, TfOH, dioxane, DCM, −40 to −20 °C,...
Scheme 4: Automated synthesis of 16. Reagents and conditions: (i) (a) NIS, TfOH, dioxane, DCM, −40 to −20 °C,...
Scheme 5: Automated synthesis of 27. Reagents and conditions: (i) (a) NIS, TfOH, dioxane, DCM, −40 to −20 °C,...
Scheme 6: Automated synthesis of 30. Reagents and conditions: (i) (a) NIS, TfOH, dioxane, DCM, −40 to −20 °C,...
Scheme 7: Reagents and conditions: (i) 10% DMF in PBS buffer pH 7.5, overnight, 80%.