Dimethylene-D-gluconic Acid

Mehltretter, C. L.; Mellies, R. L.; Rist, C. E.; Hilbert, Guido E.

doi:10.1021/ja01201a020

Cited by 15 publications

(7 citation statements)

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“…The cyclic diol 2,4 : 3,5‐di‐ O ‐methylidene‐ D ‐glucitol (gludioxol, Gx) was prepared following the chemical synthetic route depicted in Scheme . Compounds 2,4 : 3,5‐di‐ O ‐methylidene‐ D ‐gluconic acid and methyl 2,4 : 3,5‐di‐ O ‐methylidene‐ D ‐gluconate were synthesized from commercial 1,5‐ D ‐gluconolactone as described elsewhere 17…”

Section: Methodsmentioning

confidence: 99%

Carbohydrate‐based poly(ester‐urethane)s: A comparative study regarding cyclic alditols extenders and polymerization procedures

Marín

Muñoz‐Guerra

2009

J of Applied Polymer Sci

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A set of segmented poly(ester-urethane)s were prepared from diisocyanates HDI or MDI and using 1,4-butanediol and D-glucose-derived cyclic diols (1,4 : 3,6-dianhydro-D-glucitol (isosorbide) or 2,4;3,5-di-O-methylidene-D-glucitol (gludioxol) or mixtures of them) as extenders. Hydroxyl end-capped polycaprolactone with a molecular weight of 3000 gÁmol À1 was used as soft segment. Two polymerization methods, in solution and in bulk, were applied for the synthesis of these poly(ester-urethane)s. The influence of the preparation procedure and composition in cyclic extender on synthesis results, structure, and properties of the novel poly(ester-urethane)s was comparatively evaluated and discussed. The effect of replacement of 1,4-butanediol by isosorbide or gludioxol on hydrodegradability was also assessed; the hydrolysis rate increased noticeably with the presence of glucitol derived units, although degradation of the polymers took place essentially by hydrolysis of the polyester soft segment.

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Section: Methodsmentioning

confidence: 99%

Carbohydrate‐based poly(ester‐urethane)s: A comparative study regarding cyclic alditols extenders and polymerization procedures

Marín

Muñoz‐Guerra

2009

J of Applied Polymer Sci

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“…Outline of syntheses of gluconamide derivatives from gluconolactone. Reagents and conditions: i, trioxane, H 2 O-H + ; 6 ii, H + -MeOH; 7 iii, excess alkylamine; 1 iv, TsCl in pyridine, 0 °C; v, imidazole, CHCl 3 , 15 kbar, 50 °C; vi, 4-hydroxypyridine, triethylamine, 115 °C; vii, picolinoyl chloride, CHCl 3 , 0 °C; viii, benzoyl chloride, pyridine, 0 °C; ix, C 6 H 11 C(O)Cl, 0 °C. to electron microscopy grids.…”

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confidence: 99%

Organogel formation and molecular imprinting by functionalized gluconamides and their metal complexes

Hafkamp¹,

Kokke²,

Danke³

et al. 1997

Chem. Commun.

166

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“…The polyaddition reaction of diisocyanates HMDI and MDI with the alditols 2,4:3,5‐di‐ O ‐methylene‐ D ‐glucitol ( 1 ),29, 30 2,3:4,5‐di‐ O ‐methylene‐galactitol ( 2 ),31 and 2,4:3,5‐di‐ O ‐isopropylidene‐ D ‐mannitol ( 3 ),32 was found to be an effective procedure for the preparation of the acetalized sugar‐derived polyurethanes PU(MenGlu‐HMDI) , PU(MenGlu‐MDI) , PU(MenGa‐HMDI) , PU(MenGa‐MDI) , PU(DipMa‐HMDI) , and PU(DipMa‐MDI) (Scheme ). The reaction was carried out in DMF solution under mild conditions and using dibutyltin (II) dilaurate as catalyst.…”

Section: Resultsmentioning

confidence: 99%

“…This was prepared from 2,4:3,5‐di‐ O ‐methylene‐ D ‐glucitol ( 1 )29, 30 (175 mg and 0.84 mmol) in dry DMF (3 mL), HMDI (140 μL and 0.84 mmol) and dibutyltin (II) dilaurate (2% w/w). The mixture was stirred at 60 °C, and worked‐up as described above in the general procedure.…”

Section: Methodsmentioning

confidence: 99%

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Conformationally restricted linear polyurethanes from acetalized sugar‐based monomers

Begines

Zamora

Benito

et al. 2012

J. Polym. Sci. A Polym. Chem.

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Linear polyurethanes based on sugar monomers having D-gluco, galacto, and D-manno configurations and their secondary hydroxyl groups protected as bicyclic acetals, have been prepared by polyaddition reaction of these diol monomers to hexamethylene diisocyanate (HMDI) and 4,4 0 -methylenebis(phenyl isocyanate) (MDI). The new polyurethanes seem to be amorphous materials, except that obtained from 2,3:4,5-di-O-methylene-galactitol and HMDI. Weight-average molecular weights, determined by GPC, were in the range 16,000-115,200. TGA analyses indicated that the thermal stability of these bicyclic polyurethanes is comparable to those based on the isosorbide; both the onset and the maximum rate decomposition temperatures increased significantly with respect to the polyur-ethanes based on acyclic sugar monomers. The presence of the acetalized alditol units in the polyurethanes also increased the T g s as compared with their acyclic analogs. Deacetalization of the polyurethanes containing di-O-isopropylidene-D-mannitol units yielded the polyhydroxylated polymers in good yields, without apparent degradation of the polymer chain. These hydroxylated polymers showed an enhanced hydrophilicity and degradability and lower T g s and thermal stability than their parent acetalized polyurethanes. V C 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 50: [4638][4639][4640][4641][4642][4643][4644][4645][4646] 2012

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Dimethylene-D-gluconic Acid

Cited by 15 publications

References 0 publications

Carbohydrate‐based poly(ester‐urethane)s: A comparative study regarding cyclic alditols extenders and polymerization procedures

Carbohydrate‐based poly(ester‐urethane)s: A comparative study regarding cyclic alditols extenders and polymerization procedures

Organogel formation and molecular imprinting by functionalized gluconamides and their metal complexes

Conformationally restricted linear polyurethanes from acetalized sugar‐based monomers

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