A simple approach to 5,5′-bis(1,3-dioxolan-4-ones) of tartaric acids

Markert, Morris; Buchem, I.; Krüger, Hannes; Mahrwald, Rainer

doi:10.1016/j.tetasy.2003.12.016

Cited by 6 publications

(5 citation statements)

References 11 publications

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“…The insoluble material was collected by filtration and dried in vacuum to afford pure 6 (1.72 g, 60%) as a snow-white solid. NMR data were essentially identical to those reported in the literature …”

Section: Methodssupporting

confidence: 80%

“…We then turned our attention to the optically active analogue 8 . Direct preparation of the requisite bis(acetal) starting material 6 from tartaric acid using lithium perchlorate as a promoter has been reported . However, in the case of sterically bulky trimethylacetaldehyde, we find this reaction to be somewhat sluggish, possibly reflecting the back reaction with water.…”

mentioning

confidence: 69%

“…13 C NMR (CDCl 3 ): δ 23.2, 34.3, 73.0, 110.1, 169.6. Melting point sample was crystallized from hot 2:1 heptane/ethyl acetate, mp 152 °C (lit . 136−138 °C).…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of Z-5-Carboxymethylene-1,3-dioxolan-4-ones: A Better Way

et al. 2007

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The title compounds were prepared by a straightforward two-step procedure. Tartaric acid was first protected as either a bis(ketal) or a bis(acetal). This intermediate was then treated with potassium tert-butoxide at reduced temperature to effect a stereoselective elimination leading to the Z diastereomer of the alpha,beta-unsaturated acid. This protocol is useful for the laboratory-scale synthesis of these compounds but can also be scaled up to produce kilogram quantities of the material.

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Section: Methodssupporting

confidence: 80%

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confidence: 69%

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Synthesis of Z-5-Carboxymethylene-1,3-dioxolan-4-ones: A Better Way

et al. 2007

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“…The selective differentiation of the tartrate esters was challenging (Scheme ). A dioxolanone intermediate was prepared by hydrolyzing 13 with an NaOH solution and treating the resulting product with an excess of 2,2-dimethoxy propane and a catalytic amount of PTSA . The crude mixture was then dissolved in DMF and reacted with Cs 2 CO 3 and isopropyl iodide to give 28 .…”

mentioning

confidence: 99%

“…A dioxolanone intermediate was prepared by hydrolyzing 13 with an NaOH solution and treating the resulting product with an excess of 2,2-dimethoxy propane and a catalytic amount of PTSA. 27 The crude mixture was then dissolved in DMF and reacted with Cs 2 CO 3 and isopropyl iodide to give 28. Hydrolysis of the latter with AcOH in water at 50 °C and treatment with TMSCH 2 N 2 provided 31.…”

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confidence: 99%

Acyclic Tethers Mimicking Subunits of Polysaccharide Ligands: Selectin Antagonists

Calosso

Tambutet

Charpentier

et al. 2014

ACS Med. Chem. Lett.

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We report on the design and synthesis of molecules having E- and P-selectins blocking activity both in vitro and in vivo. The GlcNAc component of the selectin ligand sialyl Lewis(X) was replaced by an acyclic tether that links two saccharide units. The minimization of intramolecular dipole-dipole interactions and the gauche effect would be at the origin of the conformational bias imposed by this acyclic tether. The stereoselective synthesis of these molecules, their biochemical and biological evaluations using surface plasmon resonance spectroscopy (SPR), and in vivo assays are described. Because the structure of our analogues differs from the most potent E-selectin antagonists reported, our acyclic analogues offer new opportunities for chemical diversity.

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