Download e-book for iPad: Advances in Carbohydrate Chemistry and Biochemistry by Derek Horton (Eds.)

By Derek Horton (Eds.)

ISBN-10: 0123808561

ISBN-13: 9780123808561

On the grounds that its inception in 1945, this serial has supplied critical articles written by way of study experts that combine commercial, analytical, and technological points of biochemistry, natural chemistry, and instrumentation technique within the examine of carbohydrates.Contributions from best professionals and specialists Informs and updates on the entire most recent advancements within the box

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73 described the use of this material as activator for O-glycosidation of glycals with several alcohols under mild conditions. For example, glycosidation of 3,4-di-Oacetyl-L-rhamnal (43) with alcohols 35–40 in dichloromethane, using 30% (w/w) of catalyst gave products of allylic rearrangement in high yield, with moderate to good a-stereoselectivity (Schemes 7 and 9). 74,75 have shown that montmorillonite K-10 also induces the Ferrier rearrangement of glycals when conducted with microwave irradiation.

ZEOLITES AND OTHER SILICON-BASED PROMOTERS 49 The results obtained by using this reagent system are comparable to those achieved using such alternative catalysts as Sc(OTf)3, Yb(OTf)3, CAN, and BF3Á Et2O, and even better in some cases, in terms of yield, reaction time, and anomeric selectivity. 83 also reported the Ferrier rearrangement of 3,4,6-tri-O-acetyl-D-glucal and -galactal with several alcohols, including monosaccharides, and thiols, bearing allyl, propargyl, isopropylidene, benzyl, and isopropyl groups.

The sequential glycosylations were performed at À 40  C using NIS and H2SO4–SiO2, and the acetylated trisaccharide, lacking the TBDMS group, was obtained after raising the temperature to ambient. 90 Other glycoconjugates were synthesized by H2SO4–SiO2-promoted glycosylation methodologies. 91 Glycosylation of a rhamnosyl acceptor at C-3 with the known p-tolyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D-glucopyranoside, activated by NIS in the presence of H2SO4–SiO2, afforded the disaccharide precursor of 79 in 91% yield.

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


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