Versatile building blocks from disaccharides: glycosylated 5-hydroxymethylfurfurals

Martin, Dierk; Lichtenthaler, Frieder W.

doi:10.1016/j.tetasy.2005.12.010

Cited by 23 publications

(20 citation statements)

References 33 publications

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“…1 revealed that the diglucosyl substitution was at the methylene of 5-HMF. By comparing the 1D and 2D (COSY, NOESY, HMQC, and HMBC) NMR spectroscopic data and prior literature [11][12][13], 1 was assigned as 5-(a-D-glucopyranosyl-(1?6)-a-D-glucopyranosyloxymethyl)-2-furancarboxaldehyde.…”

Section: Resultsmentioning

confidence: 98%

5-Hydroxymethyl-2-furfural, a clinical trials agent for sickle cell anemia, and its mono/di-glucosides from classically processed steamed Rehmanniae Radix

et al. 2007

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Rehmanniae Radix (Di Huang) is one of the most important traditional Chinese medicines (TCM), and is used for multiple therapeutic purposes. In our investigation of the chemical constituents of Rehmanniae Radix, steamed roots were prepared by the classical processing method. Reversed-phase HPLC of the 50% MeOH extract of steamed Rehmanniae Radix yielded three 5-hydroxymethylfurfural derivatives. The new furfural disaccharide 5-(alpha-D-glucopyranosyl-(1-->6)-alpha-D-glucopyranosyloxymethyl)-2-furancarboxaldehyde (1) was isolated and characterized, together with its known aglycone 5-hydroxymethyl-2-furfural (3), which is currently in sickle cell anemia Phase I clinical trials, and its corresponding monosaccharide 5-(alpha-D-glucopyranosyloxymethyl)-2-furancarboxaldehyde (2), which was isolated as a natural product for the first time. The presence of these three compounds, particularly 3, which were not found in the unprocessed extract of Rehmanniae Radix, could substantiate the traditional medicinal use of steamed Rehmanniae Radix.

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Section: Resultsmentioning

confidence: 98%

5-Hydroxymethyl-2-furfural, a clinical trials agent for sickle cell anemia, and its mono/di-glucosides from classically processed steamed Rehmanniae Radix

et al. 2007

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“…Furan is an attractive compound because it is chemically obtainable through the catalytic decarbonylation of furfural, which is obtained through chemical modification of hemicelluloses (i.e., xylose) . Functional furan derivatives, such 5‐hydroxymethylfurfural, are prepared through the dehydration of glucose . The major source of glucose is in vegetable products like corn, which is an abundant renewable resource.…”

Section: Introductionmentioning

confidence: 99%

The effect of furan molecular units on the glass transition and thermal degradation temperatures of polyamides

Cureton

Napadensky

Annunziato

et al. 2017

J of Applied Polymer Sci

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Interfacial polymerization is used to prepare biobased furan polyamides from the carbohydrate‐derived monomer, 2,5‐furan dicarboxylic acid, aromatic diamines, and varying chain length aliphatic diamines. The molecular weights of the furan polyamides variations range 10,000–70,000 g/mol. These biobased polyamides have improved solubility relative to petroleum‐derived polyamides affording enhanced processability options. The glass transition temperatures (Tg) of the biobased furan polyamides are higher than that of aliphatic analogs, but lower than phenyl‐aromatic analogs. The Tg for these furan polyamides are as high as 280 °C. Also, the furan polyamide glass transition temperatures increase with decreasing aliphatic diamine chain length similar to results exemplified in petroleum‐based nylons. Group contribution parameters are determined for furans to enable simple prediction of the glass transition temperature and decomposition temperature of furan polyamides. The molar glass transition function for the furan is calculated to be 27.6 ± 1.5 K kg/mol. Thermal analysis measurements of the biobased furan polyamides have maximum thermal degradation temperatures at 350 °C or higher, similar to that of aliphatic polyamides when scaled with the number average molecular weight. The molar decomposition temperature functions are determined to be 37 K kg/mol for furans bonded to aliphatic units and 42 K kg/mol for furans bonded to phenyl units. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 45514.

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“…Such intermediates would not lead to C-2 epimerisation for aldoses with threo configuration at C-2-C-3, 19,21 the lack of such epimerisation of galactose, 6-deoxygalactose and arabinose has been shown, 21 and no mannose or glucosylmannoses were observed from glucose 19 or reducing glucosylglucoses 34 in aqueous aluminate solution. There has been much discussion about the mechanism of the Lobry de Bruyn-Alberda van Ekenstein transformation for more than 60 years.…”

Section: Resultsmentioning

confidence: 99%

Aldose–ketose interconversion in pyridine in the presence of aluminium oxide

Ekeberg

Morgenlie

Stenstrøm

2007

Carbohydrate Research

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Versatile building blocks from disaccharides: glycosylated 5-hydroxymethylfurfurals

Cited by 23 publications

References 33 publications

5-Hydroxymethyl-2-furfural, a clinical trials agent for sickle cell anemia, and its mono/di-glucosides from classically processed steamed Rehmanniae Radix

5-Hydroxymethyl-2-furfural, a clinical trials agent for sickle cell anemia, and its mono/di-glucosides from classically processed steamed Rehmanniae Radix

The effect of furan molecular units on the glass transition and thermal degradation temperatures of polyamides

Aldose–ketose interconversion in pyridine in the presence of aluminium oxide

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