Advances in Carbohydrate Chemistry and Biochemistry by Derek Horton (Eds.)

By Derek Horton (Eds.)

Due to the fact that its inception in 1945, this serial has supplied critical articles written through examine experts that combine commercial, analytical, and technological facets of biochemistry, natural chemistry, and instrumentation method within the examine of carbohydrates.Contributions from top specialists and specialists Informs and updates on all of the most modern advancements within the box

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69 The glucosylation of butanol was performed over K-10, KSF, and KSF/O montmorillonites, showing that the rate and the efficiency of the transformation depended on the relative acidity of the catalysts. Hence, the highest glucose conversion (88%) and the best product yield (78%) were achieved for the catalyst possessing the strongest acid character. The catalytic activity was ascribed to the transfer of acidity from the solid to the liquid phase and was detected by measuring the pH of the solvent after removal of the clay suspension by filtration.

P. RAUTER ET AL. and the target molecules were obtained in moderate yield (24 and 26 in 46% and 50% yields, respectively), while the glycosylflavonoid 25 was recovered in only 38% yield. The a-selectivity observed in these catalytic transformations arises from the well-known anomeric effect. This new methodology for synthesis of 2,3-unsaturated glycosyl derivatives involves zeolites-promoted debenzoxylation at position 3, thus expanding the synthetic use of the Ferrier rearrangement to benzyl-protected glycals.

Synthesis of terpenoid glucosides via a stereoselective glucosidation of a 1,2-anhydro sugar catalyzed by silica gel. conditions and, unlike other acid catalysts, silica gel led to good regioselectivity. However, glucosylation of the sterically hindered trans- and cis-carveol gave low yields of 52e and 52f, respectively. Further deprotection afforded the terpenoid glucosides 53d, 53f, and 54. Silica-supported reagents have been exploited as nontoxic, inexpensive, reusable, and environmentally acceptable catalysts for developing stoichiometric reaction methods in organic chemistry and specifically in carbohydrate chemistry.

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