NEW RESULTS ON THE BENZYLATION OF SATURATED MONO- AND DISACCHARIDES—A SEMIEMPIRICAL STUDY

REFERENCES

• Hamann , C. H. , Pleus , S. , Koch , R. and Barghorn , K. 1999 . Semiempirical study on the substitution mechanism of carbohydrates . J. Carbohydr. Chem. , 18 ( 2 ) : 1051 – 1065 .
   Web of Science ®Google Scholar
• Fischer , S. and Hamann , C. H. 1995 . The alkylation and acylation of glycals via an initializing electrochemical step . J. Carbohydr. Chem. , 14 ( 3 ) : 327 – 339 .
   Web of Science ®Google Scholar
• Blackburne , I. D. , Burfitt , A.I. R. , Fredericks , P. F. and Guthrie , R. D. 1976 . Studies on unsaturated sugars with particular reference to the synthesis of 6-deoxy-6-fluoro derivatives . Aust. J. Chem. , 29 : 381 – 391 .
   Web of Science ®Google Scholar
• Stewart , J.J. P. 1993 . MOPAC 93. QCPE 455, Version 93
   Google Scholar
• Dewar , M.J. S. and Thiel , W. 1977 . Ground states of molecules. 38. The MNDO method. Approximations and parameters . J. Am. Chem. Soc. , 99 ( 15 ) : 4899 – 4917 .
   Web of Science ®Google Scholar
• Dewar , M.J. S. , Zoebisch , E. G. , Healy , E. F. and Stewart , J.J. P. 1985 . AM1: a new general purpose quantum mechanical molecular model . J. Am. Chem. Soc. , 107 ( 13 ) : 3902 – 3909 .
   Web of Science ®Google Scholar
• Stewart , J.J. P. 1989 . Optimization of parameters for semiempirical methods I. Method . J. Comput. Chem. , 10 ( 2 ) : 209 – 220 .
   Web of Science ®Google Scholar
• Stewart , J.J. P. 1989 . Optimization of parameters for semiempirical methods II. Applications . J. Comput. Chem. , 10 ( 2 ) : 221 – 264 .
   Web of Science ®Google Scholar
• Hamann , C. H. , Fischer , S. , Polligkeit , H. and Wolf , P. 1992 . Synthetische Aspekte der Elektrochemie der Kohlenhydrate . DECHEMA Monogr. , 125 : 649 – 663 .
   Google Scholar
• Hamann , C. H. , Fischer , S. , Polligkeit , H. and Wolf , P. 1993 . The alkylation of mono- and disaccharides via an initializing electrochemical step . J. Carbohydr. Chem. , 12 ( 2 ) : 173 – 190 .
   Web of Science ®Google Scholar
• Hamann , C. H. , Fischer , S. , Polligkeit , H. , Schleif , D. and Wolf , P. 1994 . Some mechanistic aspects of carbohydrate electrochemistry . Z. Phys. Chem. , 185 : 69 – 78 .
   Web of Science ®Google Scholar
• Collins , P. M. and Ferrier , R. J. 1995 . Monosaccharides Their Chemistry and Their Roles in Natural Products 342 – 414 . England : John Wiley and Sons . ISBN 0 471 95342 3, and references therein
   Google Scholar
• Eby , R. , Webster , K. T. and Schuerch , C. 1984 . Regioselective alkylation and acylation of carbohydrates engaged in metal complexes . Carbohydr. Res. , 129 : 111 – 120 .
   PubMed Web of Science ®Google Scholar
• Flowers , H. M. 1982 . Partial benzylation of methyl α-l-fucopyranoside . Carbohydr. Res. , 99 : 170 – 174 .
   Web of Science ®Google Scholar
• Flowers , H. M. 1982 . Selective benzylation of some d-galactopyranosides . Carbohydr. Res. , 100 : 418 – 423 .
   Web of Science ®Google Scholar
• Koto , S. , Takebe , Y. and Zen , S. 1972 . The Synthesis of methyl 2,4,6-tri-O-benzyl-α-d-glucopyranoside . Bull. Chem. Soc. Jpn. , 45 : 291 – 293 .
   Google Scholar
• Koto , S. , Takenaka , K. , Morishima , N. , Sugimoto , A. and Zen , S. 1984 . A simple synthesis of methyl 2,3,6- and 2,4,6-tri-O-benzyl-α-d-mannosides . Bull. Chem. Soc. Jpn. , 57 : 3603 – 3604 .
   Google Scholar
• Morishima , N. , Koto , S. , Oshima , M. , Sugimoto , A. and Zen , S. 1983 . Partial benzylation of methyl α- and β-d-galactopyranosides . Bull. Chem. Soc. Jpn. , 56 : 2849 – 2850 .
   Google Scholar
• Garegg , P. J. , Iversen , T. and Oscarson , S. 1976 . Monobenzylation of diols using phase-transfer catalysis . Carbohydr. Res. , 50 : C12 – C14 .
   Web of Science ®Google Scholar
• Haque , M. E. , Kikuchi , T. , Yoshimoto , K. and Tsuda , Y. 1985 . Regioselective monoalkylation of non-protected glycopyranosides by the dibutyltin oxide method . Chem. Pharm. Bull. , 33 : 2243 – 2255 .
   Web of Science ®Google Scholar
• Küster , J. M. and Dyong , L. 1975 . Synthesen aller methyl-mono-, methyl-di-und methyl-tri-O-benzyl-α-d-glucopyranoside . Liebigs Ann. Chem. , : 2179 – 2189 .
   Google Scholar
• Chauvin , C. , Baczko , 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
• Reinfeld , E. and Heincke , K. D. 1971 . Selektive O-alkylierung von Saccharose . Chem. Ber. , 104 : 265 – 269 .
   Google Scholar
• Inoue , Y. and Nagasawa , K. 1987 . Methylation of methyl α-d-hexopyranosides with diazomethane in the presence of a small amount of water . Carbohydr. Res. , 168 : 181 – 190 .
   Google Scholar
• Handa , N. and Montgomery , R. 1969 . Partial methylation of methyl α-d-mannopyranoside. Preparation and distribution of mono-, di-, trimethyl ethers of d-mannose . Carbohydr. Res. , 11 : 467 – 484 .
   Google Scholar
• Stanek , J. 1990 . Preparation of selectively alkylated saccharides as synthetic intermediates . Top. Curr. Chem. , 156 : 209 – 256 .
   Google Scholar
• Klamt , A. and Schüürmann , G. 1993 . COSMO: A new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient . J. Chem. Soc., Perkin Trans. 2 , : 799 – 805 .
   Google Scholar
• MOPAC 2000, ©Fujitsu Limited 2000
   Google Scholar
• An overview about the evolution of the structural presentation of sucrose and also of the determination of the possible conformations of sucrose in crystal and in solution is given by Lichtenthaler, F.W., Immel, S., Kreis, U. Old Roots–New Branches: Evolution of the Structural Representation of Sucrose. In Carbohydrates as Raw Materials; Lichtenthaler, F.W., Ed., VCH-Verlagsgesellschaft mbH: d-6940 Weinheim, 1991; pp. 1–33 and references therein
   Google Scholar
• Christofides , C. and Davies , D. B. 1985 . Cooperative and competitive hydrogen bonding in sucrose determined by SIMPLE 1H NMR spectroscopy . J. Chem. Soc., Chem. Commun. , : 1533 – 1534 .
   Google Scholar
• Davies , D. B. and Christofides , J. C. 1987 . Comparison of intramolecular hydrogen-bonding conformations of sucrose-containing oligosaccharides in solution and in the solid state . Carbohydr. Res. , 163 : 269 – 274 .
   Google Scholar
• Tran , V. H. and Brady , J. W. 1990 . Disaccharide conformational flexibility, II. Molecular dynamics simulations of sucrose . Biopolymers , 29 : 977 – 997 .
   Google Scholar