The use of boric and benzeneboronic acids in the partial acetonation of monosaccharides

Stacey, B.E.; Tierney, Brian

doi:10.1016/s0008-6215(00)83131-6

Cited by 25 publications

(6 citation statements)

References 26 publications

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“…The cyclic boronate derivatives of the compounds listed in Figure 2 showed characteristic 1 H-NMR chemical shifts for the five aromatic protons of the phenyl group bonded directly to the boron atoms [ 36 , 37 , 38 ]. The two protons ortho to the boron atom are deshielded, and resonated at δ 8.06–8.87; the two meta protons resonated at higher field, in the region δ 7.47–7.69; whilst the single para proton resonated at δ.…”

Section: Resultsmentioning

confidence: 99%

Boronate Derivatives of Functionally Diverse Catechols: Stability Studies

Ketuly

Hadi

2010

Molecules

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Section: Resultsmentioning

confidence: 99%

Boronate Derivatives of Functionally Diverse Catechols: Stability Studies

Ketuly

Hadi

2010

Molecules

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“…Thus, the yield of 9(5R/S) was decreased to 8%, while the amount of the minor products was increased (see Experimental Section); caused by activation of benzyl groups under sonochemical conditions. 5 Hz, characteristic for di-O-isopropylidene-galactopyranose derivatives [23] [24] , which generally ad-the 13 C-NMR spectra, is in the range 3:1 to 15:1. The H,H-coupling constants of the diastereomer 2 correspond to the data for 6-bromo-6deoxy-1,2:3,4-di-O-isopropylidene-α--galactopyranose [23] , whereas the couplings found for the diastereomer 3 correspond to 6-bromo-6-deoxy-1,2:3,4-di-O-isopropylidene-ß-altropyranose [23] .…”

Section: Methodsmentioning

confidence: 99%

ChemInform Abstract: Organofluorine Compounds and Fluorinating Agents. Part 19. Dithionite‐Catalyzed Addition of Perfluoroalkyl Iodides to Unsaturated Carbohydrates.

Zur

Miethchen

1998

ChemInform

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The perfluoroalkyl chains (ϪC 4 F 9 , ϪC 6 F 13 , ϪC 8 F 17 ) were ter-Compounds 9, 10, and 25 were hydrodeiodinated to the methylene derivatives 17, 18, and 27, respectively. Complete minally connected to the 5-enopyranose 1, and the 5-enofuranoses 8 and 23 by addition, in the presence of sodium dideprotection of the perfluoroalkyl-substituted pyranose 3 (prepared from 1), and of the furanoses 17 and 18 led to the thionite, of the corresponding homologous perfluoroalkyl iodides to the double bond. Up to six products were separated carbohydrate-based amphiphilic mesogens 29/30, 21, and 22, respectively, with a perfluoroalkyl tail. These formed mefrom each reaction mixture and then fully characterised. The 5-iodo derivatives 9, 10 (prepared from 8), 24, 25, and 26 sophases of the smectic A type. (prepared from 23) were diastereomeric mixtures (5R/5S). Fluorocarbons are biochemically inert, dense, have a lowWe tested several methods for the perfluoroalkylation of carbohydrates [20] with the aim of synthesizing a new group surface tension and have a very high gas dissolving capacity. For use as "artificial blood" for drug delivery and targeting, of "single tailed" amphiphilic liquid crystals. The most convenient, mild and inexpensive method seemed to be the diand for use as contrast agents, fluorocarbons have to be emulsified with water. For stable emulsions a variety of bio-thionite initiated addition of perfluoroalkyl halides to unsaturated compounds in water/acetonitrile [18] [19] , which compatible, strongly surface active fluorophilic/hydrophilic amphiphiles are needed. However, the higher the fluorine gave moderate and reproducible yields. The first applications of the dithionite initiation method in carbohydrate content of the amphiphile, the lower is its hemolytic activity [2] . Perfluoro-alkylated carbohydrates may serve as chemistry were reported by Portella and coworker [21] and Huang and coworkers [22] . We were unable to reproduce the useful emulsifiers for "water-in-fluorocarbon" emulsions intended for biomedical uses, such as drug targeting, because results of the latter; a perfluoroalkylation of triacetylglucal.Nearly no glucal reacted in the course of the reaction. Howtheir hydrophilic sugar head group may make them susceptible to recognition by specific receptors [3] [4] . In most of the ever, the addition of some perfluoroalkyl iodides to unsaturated monosaccharides with an exocyclic double bond in perfluoroalkyl-substituted carbohydrate amphiphiles which are already known, the perfluoroalkyl chain is attached to the 5-position did prove successful. Thus, the enopyranose 1 was reacted with perfluorohexyl iodide in the presence of the carbohydrate via a hydrocarbon spacer and an ester, ether, amide, or phosphate bond [4] [5] . In this paper we re-sodium dithionite to give a product mixture (compounds 2Ϫ7), where the perfluoroalkyl chain is regioselectively atport on the syntheses of carbohydrate-based perfluoroalkyl amphiphiles, where the perfluoroalkyl chain is directly at-tached to the 6-po...

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“…Thus O, N, P and also S atoms can coordinate to a boron atom to obtain various structures. 12,3,4,9,13,14 In addition, since boron has a similar atomic size to carbon, it allows us to investigate alloying experiments on the hydrogenation properties of TiFe. 15 Biological research has also increased over last few decades due to its application in cancer treatment.…”

Section: Introductionmentioning

confidence: 99%

“…H NMR (at 400.1 MHz), and13 C NMR (at 100.6 MHz) spectra were recorded on a Bruker Avance 400 spectrometer, with TMS (tetramethylsilane) as an internal reference. The IR spectra were recorded on a Mattson 1000 ATI UNICAM FT-IR spectrometer as KBr pellets.…”

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confidence: 99%