Crystal structure of [(2R,3R,4S)-3,4-bis(acetyloxy)-5-iodo-3,4-dihydro-2H-pyran-2-yl]methyl acetate

Zukerman-Schpector, Júlio; Caracelli, Ignez; Stefani, Hélio A.; Shamim, Anwar; Tiekink, Edward R. T.

doi:10.1107/s205698901402564x

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“…It was possible to crystallize compound 13 by keeping its concentrated solution in ethyl acetate at 4 °C for 48 hours. 66 The crystal system of this compound was found to be orthorhombic with P212121 space group ( Figure 29). Table 4).…”

Section: Synthesis Of 126-and 146-tris-triazolyl Glycoside Derivamentioning

confidence: 99%

“…IR (cm -1 , film) 3110, 2960, 2930, 1743, 1629, 1523, 1434, 1371, 1220, 1182, 1048, 1030, 955, 912, 786. 1 H NMR (300 MHz, CDCl3) δ 7.30 (dd, J = 3.0, 1.2 Hz, 1H), 7.17 (dd, J = 5.0, 3.0 Hz, 1H), 6.98 (dd, J = 5.0, 1.2 Hz, 1H), 6.85 (d, J = 1.1 Hz, 1H), 5.52 (d,J = 5.5 Hz,1H),5.16 (dd,J = 6.8,5.4 Hz,1H),4.36 (dd,J = 11.8,6.0 Hz,1H),4.28 (td,J = 6.4,2.9 Hz,4H),4.14 (dd,J = 11.8,3.0 Hz, 1H), 2.04 -2.00 (m, 9H). 13 C NMR (75 MHz,CDCl3) δ 170.40,170.07,169.36,150.47,129.63,128.18,125.32,122.11,97.09,85.19,82.88,74.36,67.27,66.48,61.10,20.78,20.72,20.64 Colorless oil.…”

Section: Diacetate (14i)mentioning

confidence: 99%

“…these cardiotonic effects certain amounts of cardiac glycosides have been historically used and are still being clinically used for the treatment of chronic heart failure and arrhythmias. 6 Some cardiac glycosides have shown neuroprotective activity against ischemic stroke and there are examples of cardiac glycosides used clinically for congestive heart failure ( Figure 4). 7 Glycosides are very important compounds and play key roles in living organisms for example food is stored in the form of glycosides, poisons usually are bound to a carbohydrate molecule to be eliminated from the body, they act as cellular adhesives and many others are used as medications.…”

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Funcionalização de 3,4,6-tri-O-acetil-D-glucal via click chemistry e reações de acoplamento cruzado catalizado por paládio

Shamim¹

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Functionalization of 3,4,6-triO -acetyl-D-glucal has been performed using crosscoupling (Sonogashira and Stille) reactions, azide-alkyne cycloadditions (Click chemistry) and electrophile-promoted nucleophilic alkyne cyclizations. Using these reactions along with the already reported functional group transformations (FGT) and Ferrier rearrangement reactions, libraries of glucal-based compounds were synthesized with members of characteristic photophysical and potential biological properties. In the first part, the synthesis of libraries of bis-and tris-triazolyl glycosyl derivatives is described starting from 3,4,6-triO -acetyl-D-glucal using the above-mentioned reactions. In the second part of this work, the synthesis of a library of 2-alkynyl glucal derivatives using a copper and ligand-free Sonogashira coupling, followed by synthetic applications of these glucal alkynes is reported. Palladium-catalyzed regioselective hydrostannation of these 2-alkynyl glucals was performed using tributyltin hydride to generate a library of regioisomeric stannyl derivatives of glucal. Moreover, these 2alkynyl glucal derivatives synthesized in the first part were also used in electrophilepromoted nucleophilic 5-endo-dig cyclization to afford bicyclic glucal derivatives. In the final part, the use of stannyl derivatives of glucal to synthesize libraries of substituted 2-alkenyl glucal derivatives is described. This part also includes certain functional group transformations and cross-couplings (Stille and Sonogashira) as well as click chemistry to generate libraries of alkynyl and triazolyl substituted 2-alkenyl-Dglucal derivatives. In most of the cases, the products were obtained in very good to excellent yields and were analyzed using 1 H NMR, 13 C NMR, FTIR, HRMS, and other analytic techniques where applicable.

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Section: Synthesis Of 126-and 146-tris-triazolyl Glycoside Derivamentioning

confidence: 99%

Section: Diacetate (14i)mentioning

confidence: 99%

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