Novel unsaturated sucrose ethers and their application as monomers

Molecules

Volumn 13, Issue 4, 2008, Pages 762-770

  Crucho, Carina C ^a   Petrova, Krasimira T ^a   Pinto, Rui C ^a   Barros, Maria T ^a  

^a UNIVERSIDADE NOVA DE LISBOA   (Portugal)

Author keywords

Biodegradable copolymers; Free radical copolymerisation; Natural products copolymers; Sustainable chemistry; Vinyl sucrose ether monomers

Indexed keywords

ETHER DERIVATIVE; SUCROSE; TOLUENE;

ARTICLE; CHEMISTRY; SOLUTION AND SOLUBILITY; SYNTHESIS;

ETHERS; SOLUTIONS; SUCROSE; TOLUENE;

EID: 43049133240     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules13040762     Document Type: Article

References (22)

1. Lichtenthaler, F. W.; Peters, S., Carbohydrates as green raw materials for the chemical industry. Compt. Rend. Chim. 2004, 7, 65-90.
2. Queneau, Y.; Jarosz, S.; Lewandowski, B.; Fitremann, J., Sucrose chemistry and applications of sucrochemicals. Adv. Carbohydr. Chem. Biochem. 2008, 61, 217-292
3. Jhurry, D.; Deffieux, A.; Fontanille, M., Sucrose based polymers. Linear polymers with sucrose side-chains. Makromol.Chem. 1992, 193, 2997-3007.
4. Satomi, M.; Sogawa, S., Hard coating layer for coated products useful in pharmaceuticals and foodstuffs, contains sugar, and reduced amylolysis product containing sugar composition of hydrogenated saccharides with varying polymerization degree. JP2007053952-A, 2007.
5. Popplewell, L. M.; Henson, L., Method useful to deliver active ingredient to cleaning composition involves preparing structured material of hydrophilic particle, hydrophobic active ingredient and polyhydric material; and providing the structured material into composition. US2007048339-A1, 2007.
6. Galgali, P.; Varma, A. J.; Puntambekar, U. S.; Gokhale, D. V., Towards biodegradable polyolefines: strategy of anchoring minute quantities of monosaccharides and disaccharides onto functionalized polystyrene, and their effect on facilitating polymer biodegradation. Chem. Commun. 2002, 2884-2885.
7. Tokiwa, Y.; Fan, H.; Hiraguri, Y.; Kurane, R., Biodegradation of a sugar branched polymer consisting of sugar, fatty acid, and poly(vinyl alcohol). Macromolecules 2000, 33, 1636-1639.
8. Barros, M. T.; Petrova, K.; Ramos, A. M., Regioselective Copolymerization of Acryl Sucrose monomers. J. Org. Chem. 2004, 69, 7772-7775.
9. Barros, M. T.; Petrova, K. T.; Ramos, A. M., Biodegradable Polymers based on α- or β-Pinene and Sugar Derivatives or Styrene, Obtained under Normal Conditions and Microwave Irradiation. Eur. J. Org. Chem. 2007, 1357-1363.
10. Barros, M. T.; Maycock, C. D.; Rodrigues, P.; Thomassigny, C., Improved anomeric selectivity for the aroylation of sugars. Carbohydr. Res. 2004, 339, 1373-1376.
11. Andrade, M. M.; Barros, M. T., Facile conversion of O-sylil protected sugars into their corresponding formates using POCl3.DMF complex. Tetrahedron 2004, 60, 9235-9243.
12. Barros, M. T.; Maycock, C. D.; Sineriz, F.; Thomassigny, C., Fast galloylation of a sugar moiety: preparation of three monogalloylsucroses as references for antioxidant activity. A method for the selective deprotection of tert-butyldiphenylsilyl ethers. Tetrahedron 2000, 56, 6511-6516.
13. Barros, M. T.; Sineriz, F., Synthesis of optically active monomers and copolymers derived from protected 6′-O-acryloyl sucroses. Synthesis 2002, 10, 1407-1411.
14. Andrade, M. M.; Barros, M. T.; Rodrigues, P., Selective Synthesis Under Microwave Irradiation of Carbohydrate Derivatives Containing Unsaturated Systems. Eur. J. Org. Chem. 2007, 3655-3668.
15. Fanton, E.; Fayet, C.; Gelas, J.; Deffieux, A.; Fontanille, M.; Jhurry, D., Synthesis of 4-O- and 6-O-monoacryloyl derivatives of sucrose by selective hydrolysis of 4,6-O-(1-ethoxy-2-propenylidene)sucrose. Polymerisation and copolymerisation with styrene. Carbohydr. Res. 1993, 240, 143-152.
16. Potier, P.; Bouchou, A.; Descotes, G.; Queneau, Y., Proteinase N-catalysed transesterifications in DMSO-water and DMF-water: preparation of sucrose monomethacrylate. Tetrahedron 2000, 41, 3597-3600.
17. Jarosz, S.; Mach, M., Regio- and Stereoselective Transformations of Sucrose at the Terminal Positions. Eur. J. Org. Chem. 2002, 769-780.
18. Gu, Y.; Azzouzi, A.; Pouilloux, Y.; Jerome, F.; Barrault, J., Heterogeneously catalyzed etherification of glycerol: new pathways for transformation of glycerol to more valuable chemicals. Green Chem. 2008, 10, 164-167.
19. Gassman, P. G.; Burns, S. J.; Pfister, K. B., Synthesis of cyclic and acyclic enol ethers (vinyl ethers). J. Org. Chem. 1993, 58, 1449-1457.
20. Hughes, K. D.; Nguyen, T.-L. N.; Dyckman, D.; Dulay, D.; Boyko, W. J.; Giuliano, R., Synthesis of vinyl alpha-D-glucopyranosides from mixed acetal glycosides. Tetrahedron: Asymmetry 2005, 16, 273-282.
21. Lichtenthaler, F. W.; Immel, S.; Kreis, U. Carbohydrates as Organic Raw Materials. VCH Verlagsgessellschaft mbH: Weinheim, 1991;Chapter 1, pp.1-32.
22. Perrin, D. D.; Armagedo, W. L. F.; Perrin, D. R., Purification of Laboratory Chemicals, 2nd Ed. Pergamon Press Ltd.: New York, 1980.