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

References

• Lichtenthaler , F. W. , ed. 1991 . Carbohydrates as Organic Raw Materials Vol. 1 , Weinheim : VCH .
   Google Scholar
• Descotes , G. , ed. 1993 . Carbohydrates as Organic Raw Materials Vol. 2 , Weinheim : VCH .
   Google Scholar
• van Bekkum , H. , Röper , H. and Voragen , A. G.J. , eds. 1996 . Carbohydrates as Organic Raw Materials Vol. 3 , Weinheim : VCH .
   Google Scholar
• Praznik , W. and Huber , A. , eds. 1998 . Carbohydrates as Organic Raw Materials Vol. 4 , Vienna : WUV‐Univ. .
   Google Scholar
• Godshall , M. A. 2001 . Future directions for the sugar industry . Int. Sugar J. , 103 : 378 – 384 .
   Web of Science ®Google Scholar
• Hickson , J. L. , ed. 1977 . Sucrochemistry , ACS Symposium Series Vol. 41 , American Chemical Society . Washington, DC
   Google Scholar
• Kosaka , T. and Yamada , T. New plant and new applications of sucrose esters . American Chemical Society , 84 – 96 .
   PubMedGoogle Scholar
• Bobichon , L. A sugar ester process and its applications in calf feeding and human food additives . 115 – 120 .
   Google Scholar
• Seib , P. A. , Hoover , W. J. and Tsen , C. C. Sucrose esters in bakery foods . American Chemical Society , 121 – 135 .
   PubMedGoogle Scholar
• Simon , P. , Veyrat , S. , Piquemal , P. , Montastier , C. , Goffin , V. and Pierard , G. E. 1998 . Surfactants and the skin: the revival of sugar esters . Cosmet. Toilet. Mag. , 113 Sept. : 69 – 72 .
   Google Scholar
• Hurford , J. R. 1980 . “ Surface active agents derived from some selected disaccharides ” . In Developments in Food Carbohydrates Edited by: Lee , C. K. Vol. 2 , 327 – 350 . England : Applied Science Publishers, Ltd. .
   Google Scholar
• Muller , A.‐S. , Gagnaire , J. , Queneau , Y. , Karaoglanian , M. , Maitre , J.‐P. and Bouchu , A. 2002 . Winsor behaviour of sucrose fatty acid esters: choice of the cosurfactant and effect of the surfactant composition . Colloids Surf., A Physicochem. Eng. Asp. , 203 : 55 – 66 .
   Web of Science ®Google Scholar
• Thevenin , M. A. , Grossiord , J. L. and Poelman , M. C. 1996 . Sucrose esters/cosurfactant microemulsions systems for transdermal delivery: assessment of bicontinuous structures . Int. J. Pharm. , 137 : 177 – 186 .
   Web of Science ®Google Scholar
• Garti , N. , Clement , V. , Leser , M. , Aserin , A. and Fanun , M. 1999 . Sucrose ester microemulsions . J. Mol. Liq. , 80 ( 2–3 ) : 253 – 296 .
   Web of Science ®Google Scholar
• Husband , F. A. , Sarney , D. B. , Barnard , M. J. and Wilde , P. J. 1998 . Comparison of foaming and interfacial properties of pure sucrose monolaurates, dilaurate and commercial preparations . Food Hydrocoll. , 12 : 237 – 244 .
   Web of Science ®Google Scholar
• Söderman , O. and Johansson , I. 2000 . Polyhydroxyl‐based surfactants and their physicochemical properties and applications . Curr. Opin. Colloid Interface Sci. , 4 : 391 – 401 .
   Web of Science ®Google Scholar
• Polat , T. and Linhardt , R. J. 2001 . Synthesis and applications of sucrose‐based esters . J. Surfactants Deterg. , 4 : 415 – 421 .
   Web of Science ®Google Scholar
• Thévenet , S. , Descotes , G. , Bouchu , A. and Queneau , Y. 1997 . Hydrophobic effect driven esterification of sucrose in aqueous medium . J. Carbohydr. Chem. , 16 ( 4–5 ) : 691 – 696 .
   Web of Science ®Google Scholar
• Salanski , P. , Descotes , G. , Bouchu , A. and Queneau , Y. 1998 . Monoacetalation of unprotected sucrose with citral and ionones . J. Carbohydr. Chem. , 17 ( 1 ) : 129 – 142 .
   Web of Science ®Google Scholar
• Descotes , G. , Gagnaire , J. , Bouchu , A. , Thévenet , S. , Giry‐Panaud , N. , Salanski , P. , Belniak , S. , Wernicke , A. , Porwanski , S. and Queneau , Y. 1999 . Preparation of sucrose esters, ethers and acetals . Pol. J. Chem. , 73 : 1069 – 1077 .
   Google Scholar
• Gagnaire , J. , Cornet , A. , Bouchu , A. , Descotes , G. and Queneau , Y. 2000 . Competition between homogeneous and interfacial reactions during the synthesis of surfactant sucrose hydroxyalkylethers in heterogeneous medium . Colloids Surf., A , 172 : 125 – 138 .
   Web of Science ®Google Scholar
• Chauvin , C. , Baczco , K. and Plusquellec , D. 1993 . New highly regioselective reactions of unprotected sucrose. Synthesis of 2‐O‐acylsucroses and 2‐O‐(N‐alkylcarbamoyl)sucroses . J. Org. Chem. , 58 : 2291 – 2295 .
   Web of Science ®Google Scholar
• Hamann , C. H. , Fischer , S. , Polligkeit , H. and Wolf , P. 1993 . The alkylation of mono‐ and di‐saccharides via an initialising electrochemical step . J. Carbohydr. Chem. , 12 : 173 – 190 .
   Web of Science ®Google Scholar
• Lichtenthaler , F. W. , Immel , S. and Pokinskyj , P. 1995 . Molecular modeling of saccharides. Part 8. Selective 2‐O‐benzylation of sucrose: a facile entry to its 2‐deoxy‐ and 2‐keto‐derivatives and to sucrosamine . Liebigs Ann. Chem. , : 1939 – 1947 .
   Google Scholar
• Houdier , S. and Perez , S. 1995 . Assessing sucrose hydroxyl acidities through semiempirical calculations . J. Carbohydr. Chem. , 14 : 1117 – 1132 .
   Web of Science ®Google Scholar
• Giry , N. , Descotes , G. , Bouchu , A. and Queneau , Y. 1999 . Consequences of the pre‐eminent reactivity of OH‐2 in sucrose: cyclic acetalation at OH‐2 and OH‐3 under basic conditions . Eur. J. Org. Chem. , : 3393 – 3398 .
   Web of Science ®Google Scholar
• Gagnaire , J. , Toraman , G. , Descotes , G. , Bouchu , A. and Queneau , Y. 1999 . Synthesis in water of amphiphilic sucrose hydroxyalkyl ethers . Tetrahedron Lett. , 40 : 2757 – 2760 .
   Web of Science ®Google Scholar
• Thévenet , S. , Wernicke , A. , Belniak , S. , Descotes , G. , Bouchu , A. and Queneau , Y. 1999 . Esterification of unprotected sucrose with acid chlorides in aqueous medium: kinetic reactivity vs acyl‐ or alkyloxycarbonyl‐ group migrations . Carbohydr. Res. , 318 : 52 – 66 .
   Web of Science ®Google Scholar
• Queneau , Y. , Gagnaire , J. , West , J. J. , Mackenzie , G. and Goodby , J. W. 2001 . The effect of molecular shape on the liquid crystal properties of the mono‐O‐[2‐hydroxydodecyl]‐sucrose . J. Mater. Chem. , 11 : 2839 – 2844 .
   Web of Science ®Google Scholar
• Baczco , K. , Nugier‐Chauvin , C. , Banoub , J. , Thilbault , P. and Plusquellec , D. 1995 . A new synthesis of 6‐O‐acylsucroses and of mixed 6,6′‐di‐O‐acylsucroses . Carbohydr. Res. , 269 : 79 – 88 .
   PubMed Web of Science ®Google Scholar
• Chauvin , C. and Plusquellec , D. 1991 . A new chemoenzymatic synthesis of 6′‐O‐acylsucroses . Tetrahedron Lett. , 32 ( 29 ) : 3495 – 3498 .
   Web of Science ®Google Scholar
• Baczco , K. and Plusquellec , D. 1991 . Sugar chemistry without protecting groups‐III. A facile chemical synthesis of 6‐O‐acyl‐d‐glycopyranoses and methyl‐6‐O‐acyl‐d‐glycopyranosides . Tetrahedron , 47 ( 23 ) : 3817 – 3828 .
   Web of Science ®Google Scholar
• Potier , P. , Bouchu , A. , Descotes , G. and Queneau , Y. 2000 . Proteinase N‐catalysed transesterifications in DMSO‐water and DMF‐water: preparation of sucrose monomethacrylates . Tetrahedron Lett. , 41 : 3597 – 3600 .
   Web of Science ®Google Scholar
• Potier , P. , Bouchu , A. , Gagnaire , J. and Queneau , Y. 2001 . Proteinase N‐catalysed regioselective esterification of sucrose and other mono‐ and di‐saccharides . Tetrahedron: Asymmetry , 12 : 2409 – 2419 .
   Web of Science ®Google Scholar
• Immel , S. and Lichtenthaler , F. W. 1995 . The conformation of sucrose . Liebigs Ann. Chem. , : 1925 – 1937 .
   Google Scholar