318
Views
32
CrossRef citations to date
0
Altmetric
Original Articles

Transesterification of Sucrose in Organic Medium: Study of Acyl Group Migrations

, , , &
Pages 657-669 | Received 05 Mar 2003, Accepted 30 Jul 2003, Published online: 23 Feb 2007

Keep up to date with the latest research on this topic with citation updates for this article.

Read on this site (2)

Yinglai Teng, Scott G. Stewart, Yao-Wen Hai, Xuan Li, Martin G. Banwell & Ping Lan. (2021) Sucrose fatty acid esters: synthesis, emulsifying capacities, biological activities and structure-property profiles. Critical Reviews in Food Science and Nutrition 61:19, pages 3297-3317.
Read now
Zonglong Yang, Rui Xu, Fahima Ali-Rachedi, Stéphane Chambert, Nuno M. Xavier, Laurent Soulère, Mohammed Ahmar, Grahame Mackenzie, Edward J. Davis, John W. Goodby, Stephen J. Cowling & Yves Queneau. (2017) Liquid crystalline glycosteroids and acyl steroid glycosides (ASG). Liquid Crystals 44:12-13, pages 2089-2107.
Read now

Articles from other publishers (30)

Osama G. Mohamed, Akram A. Shalabi, Ali M. El Halawany, Ashootosh Tripathi & Essam Abdel-Sattar. (2024) Hexagonosides A-F: Pregnane glycosides isolated from Caralluma hexagona. Phytochemistry 217, pages 113903.
Crossref
Juan Camilo Rojas Sterling, Julieth Orduña Ortega, Gustavo Metzker, Mauricio Boscolo & Jorge Andres Mora Vargas. (2022) Fast and selective synthesis of mono-substituted sucrose methacrylate ester monomer. Carbohydrate Research 511, pages 108465.
Crossref
Jorge Andrés Mora Vargas, Julieth Orduña Ortega, Gustavo Metzker, Jesus Eliecer Larrahondo & Mauricio Boscolo. (2020) Natural sucrose esters: Perspectives on the chemical and physiological use of an under investigated chemical class of compounds. Phytochemistry 177, pages 112433.
Crossref
Asiri A. Hettikankanamalage, Robert Lassfolk, Filip S. Ekholm, Reko Leino & David Crich. (2020) Mechanisms of Stereodirecting Participation and Ester Migration from Near and Far in Glycosylation and Related Reactions. Chemical Reviews 120:15, pages 7104-7151.
Crossref
Sławomir Jarosz, Patrycja Sokołowska & Łukasz Szyszka. (2020) Synthesis of fine chemicals with high added value from sucrose: Towards sucrose-based macrocycles. Tetrahedron Letters 61:22, pages 151888.
Crossref
Jorge Andrés Mora Vargas, Julieth Orduña Ortega, Maitê Bernardo Correia dos Santos, Gustavo Metzker, Eleni Gomes & Mauricio Boscolo. (2020) A new synthetic methodology for pyridinic sucrose esters and their antibacterial effects against Gram-positive and Gram-negative strains. Carbohydrate Research 489, pages 107957.
Crossref
Lianjie Wang & Yves Queneau. 2019. Green Chemistry and Chemical Engineering. Green Chemistry and Chemical Engineering 349 383 .
Lianjie Wang & Yves Queneau. 2018. Encyclopedia of Sustainability Science and Technology. Encyclopedia of Sustainability Science and Technology 1 35 .
Xin Fang, Zhi-Guo Zhuo, Xi-Ke Xu, Ji Ye, Hui-Liang Li, Yun-Heng Shen & Wei-Dong Zhang. (2017) Cytotoxic isovaleryl sucrose esters from Ainsliaea yunnanensis: reduction of mitochondrial membrane potential and increase of reactive oxygen species levels in A549 cells. RSC Advances 7:34, pages 20865-20873.
Crossref
Josh L. Hixson, Yoji Hayasaka, Christopher D. Curtin, Mark A. Sefton & Dennis K. Taylor. (2016) Hydroxycinnamoyl Glucose and Tartrate Esters and Their Role in the Formation of Ethylphenols in Wine. Journal of Agricultural and Food Chemistry 64:49, pages 9401-9411.
Crossref
Aleksander Lie, Anne S. Meyer & Lars Haastrup Pedersen. (2014) Appearance and distribution of regioisomers in metallo- and serine-protease-catalysed acylation of sucrose in N,N-dimethylformamide. Journal of Molecular Catalysis B: Enzymatic 106, pages 26-31.
Crossref
Yongjiang Wu, Qiyuan Shi, Houliang Lei, Xuesong Liu & Lianjun Luan. (2014) Studies on the total synthesis of tenuifoliside B. Tetrahedron 70:24, pages 3757-3761.
Crossref
Marcela Dvorakova, Marie Pribylova, Radek Pohl, Marie E. Migaud & Tomas Vanek. (2012) Alkyloxycarbonyl group migration in furanosides. Tetrahedron 68:33, pages 6701-6711.
Crossref
Ruud ter Haar, Jelle Wildschut, Asaf K. Sugih, W. Bart Möller, Pieter de Waard, Carmen G. Boeriu, Hero J. Heeres, Henk A. Schols & Harry Gruppen. (2011) Proof of principle for the synthesis of hydroxy-aryl esters of glycosidic polyols and non-reducing oligosaccharides with subsequent enzymatic coupling to a tyrosine-containing tripeptide. Carbohydrate Research 346:8, pages 1005-1012.
Crossref
Sinthuwat Ritthitham, Reinhard Wimmer & Lars Haastrup Pedersen. (2011) Polar co-solvents in tertiary alcohols effect initial reaction rates and regio-isomeric ratio ranging from 1.2 to 2.2 in a lipase catalysed synthesis of 6-O- and 6′-O-stearoyl sucrose. Process Biochemistry 46:4, pages 931-935.
Crossref
Sinthuwat Ritthitham, Reinhard Wimmer, Allan Stensballe & Lars Haastrup Pedersen. (2009) Selectivity and stability of alkaline protease AL-89 in hydrophilic solvents. Journal of Molecular Catalysis B: Enzymatic 59:4, pages 266-273.
Crossref
Sinthuwat Ritthitham, Reinhard Wimmer, Allan Stensballe & Lars Haastrup Pedersen. (2009) Analysis and purification of O-decanoyl sucrose regio-isomers by reversed phase high pressure liquid chromatography with evaporative light scattering detection. Journal of Chromatography A 1216:25, pages 4963-4967.
Crossref
Lothar Brecker, Marek Mahut, Alexandra Schwarz & Bernd Nidetzky. (2009) In situ proton NMR study of acetyl and formyl group migration in mono‐ O ‐acyl D ‐glucose . Magnetic Resonance in Chemistry 47:4, pages 328-332.
Crossref
Yves Queneau, Stéphane Chambert, Céline Besset & Rouba Cheaib. (2008) Recent progress in the synthesis of carbohydrate-based amphiphilic materials: the examples of sucrose and isomaltulose. Carbohydrate Research 343:12, pages 1999-2009.
Crossref
Chih-Ming Huang, Rai-Shung Liu, Tian-Shung Wu & Wei-Chieh Cheng. (2008) Structural establishment of polygalatenosides A and B by total synthesis. Tetrahedron Letters 49:18, pages 2895-2898.
Crossref
Qinghui Wang, Shufen Zhang & Jinzong Yang. (2007) Regioselective formation of 6-O-acylsucroses and 6,3′-di-O-acylsucroses via the stannylene acetal method. Carbohydrate Research 342:17, pages 2657-2663.
Crossref
Juliette Fitremann, Yves Queneau, Jean-Paul Maître & Alain Bouchu. (2007) Co-melting of solid sucrose and multivalent cation soaps for solvent-free synthesis of sucrose esters. Tetrahedron Letters 48:23, pages 4111-4114.
Crossref
Valérie Molinier, Paul J. J. Kouwer, Juliette Fitremann, Alain Bouchu, Grahame Mackenzie, Yves Queneau & John W. Goodby. (2007) Shape Dependence in the Formation of Condensed Phases Exhibited by Disubstituted Sucrose Esters. Chemistry – A European Journal 13:6, pages 1763-1775.
Crossref
Ignacio Pérez-Victoria, Alberto Zafra & Juan Carlos Morales. (2007) Determination of regioisomeric distribution in carbohydrate fatty acid monoesters by LC–ESI-MS. Carbohydrate Research 342:2, pages 236-242.
Crossref
J. W. Goodby, V. Görtz, S. J. Cowling, G. Mackenzie, P. Martin, D. Plusquellec, T. Benvegnu, P. Boullanger, D. Lafont, Y. Queneau, S. Chambert & J. Fitremann. (2007) Thermotropic liquid crystalline glycolipids. Chemical Society Reviews 36:12, pages 1971.
Crossref
Yves Queneau, Slawomir Jarosz, Bartosz Lewandowski & Juliette Fitremann. 2007. Advances in Carbohydrate Chemistry and Biochemistry Volume 61. Advances in Carbohydrate Chemistry and Biochemistry Volume 61 217 292 .
Valérie Molinier, Paul J. J. Kouwer, Juliette Fitremann, Alain Bouchu, Grahame Mackenzie, Yves Queneau & John W. Goodby. (2006) Self‐Organizing Properties of Monosubstituted Sucrose Fatty Acid Esters: The Effects of Chain Length and Unsaturation. Chemistry – A European Journal 12:13, pages 3547-3557.
Crossref
Valérie Molinier, Bernard Fenet, Juliette Fitremann, Alain Bouchu & Yves Queneau. (2005) PFGSE–NMR study of the self-diffusion of sucrose fatty acid monoesters in water. Journal of Colloid and Interface Science 286:1, pages 360-368.
Crossref
Valérie Molinier, Juliette Fitremann, Alain Bouchu & Yves Queneau. (2004) Sucrose esterification under Mitsunobu conditions: evidence for the formation of 6-O-acyl-3′,6′-anhydrosucrose besides mono and diesters of fatty acids. Tetrahedron: Asymmetry 15:11, pages 1753-1762.
Crossref
Yves Queneau, Juliette Fitremann & Stéphane Trombotto. (2004) The chemistry of unprotected sucrose: the selectivity issue. Comptes Rendus Chimie 7:2, pages 177-188.
Crossref

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.