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4 article(s) from Pedersen, Christian Marcus

CO₂ complexation with cyclodextrins

Cecilie Høgfeldt Jessen,
Jesper Bendix,
Theis Brock Nannestad,
Heloisa Bordallo,
Martin Jæger Pedersen,
Christian Marcus Pedersen and
Mikael Bols

Beilstein J. Org. Chem. 2023, 19, 1021–1027, doi:10.3762/bjoc.19.78

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Figure 1: Structure of cyclodextrins 1–6 studied in this work.

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Figure 2: X-ray crystal structure of CO₂ bound to α-CD.

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Figure 3: TGA curve (blue) and dTGA curve (red) for CO₂-1 crystals. Two lumps are seen with the former predom...

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Figure 4: Cell used to measure vis spectra under pressure (left), structure of 7 (middle) and spectrum of 7 (...

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Figure 5: Binding of CO₂ to 1 as a function of pressure.

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Full Research Paper

Published 17 Jul 2023

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Easy access to a carbohydrate-based template for stimuli-responsive surfactants

Thomas Holmstrøm,
Daniel Raydan and
Christian Marcus Pedersen

Beilstein J. Org. Chem. 2020, 16, 2788–2794, doi:10.3762/bjoc.16.229

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Figure 1: a) The carbohydrate-based building block for the synthesis of stimuli-responsive surfactants. b) Th...

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Scheme 1: Synthesis of 5 from levoglucosan (1).

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Scheme 2: Functionalization of the building block 5β.

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Scheme 3: Hydrolysis of the ethyl esters 12 and 13.

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Scheme 4: Synthesis of compound 19 from building block 5.

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Figure 2: ¹H NMR titration of compound 19 with Zn²⁺ ions in acetonitrile-d₃.

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Figure 3: (1) 1:1 Mixture of 1-octanol/H₂O, (2) same solvent mixture with compound 19, and (3) same solvent m...

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Published 17 Nov 2020

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Synthesis of α-D-GalpN₃-(1-3)-D-GalpN₃: α- and 3-O-selectivity using 3,4-diol acceptors

Emil Glibstrup and
Christian Marcus Pedersen

Beilstein J. Org. Chem. 2018, 14, 2805–2811, doi:10.3762/bjoc.14.258

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Scheme 1: Undesired migration followed by benzylation of the 3-O-Bz GalN₃ using several different benzylation...

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Scheme 2: Simple synthesis of two acceptors and two donors from the same common and readily available buildin...

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Scheme 3: Challenging the α,3-O-selectivity with the different 6-O-protecting group variants.

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Scheme 4: Representative glycosylations with closely related systems [34,44].

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Scheme 5: Capping the free 4-OH, allowing for easier separation of mixtures obtained during glycosylation.

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Scheme 6: Pseudotrisaccharide synthesis for LTA elucidation.

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Published 08 Nov 2018

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Silyl-protective groups influencing the reactivity and selectivity in glycosylations

Mikael Bols and
Christian Marcus Pedersen

Beilstein J. Org. Chem. 2017, 13, 93–105, doi:10.3762/bjoc.13.12

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Figure 1: Silicon-protective groups typically used in carbohydrate chemistry.

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Scheme 1: Glycosylation with sulfoxide 1.

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Scheme 2: Glycosylation with imidate 4.

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Scheme 3: Glycosylation with thioglycoside 7.

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Scheme 4: In situ formation of a silylated lactosyl iodide for the synthesis of α-lactosylceramide.

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Figure 2: Comparison of the reactivity of glycosyl donors with the pK_a of the corresponding piperidinium ions....

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Figure 3: Conformational change induced by bulky vicinal protective groups such as TBS, TIPS and TBDPS. The v...

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Scheme 5: An example of a “one pot one addition” glycosylation, where 3 glucosyl donors are mixed with 2.1 eq...

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Scheme 6: Superarmed-armed glycosylation with thioglycoside 34.

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Scheme 7: One-pot double glycosylation with the conformationally armed thioglycoside 37.

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Scheme 8: Superarmed-armed glycosylation with thioglycoside 41.

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Figure 4: Donors disarmed by the di-tert-butylsilylene protective group.

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Figure 5: The influence of a 3,6-O-tethering on anomeric reactivity and glycosylation selectivity. The α-thio...

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Scheme 9: Regio- and stereoselective glycosylation using the superarmed thioglycoside donor 20.

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Scheme 10: Superarmed donors used for C-arylation and the dependence of the size of the silylethers on the ste...

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Scheme 11: β-Selective glucosylation with TIPS-protected glucosyl donors. The α-face is shielded by the bulky ...

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Scheme 12: β-Selective rhamnosylation with a conformationally inverted donor.

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Scheme 13: α-Selective galactosylation with DTBS-protected galactosyl donors.

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Scheme 14: β-Selective arabinofuranosylation with a DTBS-protected donor.

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Scheme 15: α-Selective glycosylation with a TIPDS-protected glucal donor.

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Scheme 16: Highly β-selective glucuronylation using a 2,4-DTBS-tethered donor.

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Published 16 Jan 2017

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CO2 complexation with cyclodextrins

Easy access to a carbohydrate-based template for stimuli-responsive surfactants

Synthesis of α-D-GalpN3-(1-3)-D-GalpN3: α- and 3-O-selectivity using 3,4-diol acceptors

Silyl-protective groups influencing the reactivity and selectivity in glycosylations

CO₂ complexation with cyclodextrins

Synthesis of α-D-GalpN₃-(1-3)-D-GalpN₃: α- and 3-O-selectivity using 3,4-diol acceptors