By Derek Horton (Eds.)
In view that its inception in 1945, this serial has supplied critical articles written by means of study experts that combine business, analytical, and technological points of biochemistry, natural chemistry, and instrumentation method within the learn of carbohydrates.Contributions from prime experts and specialists Informs and updates on the entire most recent advancements within the box
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P. RAUTER ET AL. 38 HO R1 R2 AcO OAc O OAc OAc H-beta zeolite 140 ЊC 13 R1 = H, R2 = OAc 1 2 14 R = OAc, R = H R1 R 15a-e R = H, CH3, OCH3, Cl, F R2 AcO R1 OAc O O R2 AcO OAc OAc O HO O R 16a–e 18a–e 17a–e 19a–e R Scheme 3. Phenols glycosylation promoted by H-beta zeolite. yields (36–46%), along with the 2-deacetylated a-glycopyranosides (18a–e, 19a–e), in 23À28% yield. Noteworthy is the fact that the latter by-products were obtained in a single-step reaction, in considerably higher yield than that previously described using multistep methods (< 12% overall yield43).
95 Bhaskar and Loganathan96 described O-peracetylation of monosaccharides, disaccharides, and methyl glycosides (94) with acetic anhydride under catalysis by acid zeolites. From the panel of zeolites tested (HY, HEMT, HZSM-5, HZSM-12, HZSM-22, and H-beta), the large-pore zeolite H-beta provided the best yields of the fully acetylated sugars, most of them being over 85% and up to 99%, with the pyranose forms 95 accounting for 66–100% of the reaction products (Scheme 22). 97 reported the acetylation of glycerol with acetic acid performed over different solid acids, including montmorillonite K-10 and such acid zeolites as HZSM-5 and HUSY.
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. ˚ are small-pore zeolites (ii) Small-Pore Zeolites. Molecular sieves 3, 4, and 5 A (zeolites A) and have been employed, also in their acid-washed (AW) form, together with a variety of catalysts to ensure higher yields in glycosylation reactions. 59 The role of the MS is mainly to stabilize the promoters, acting as a water and/or proton scavenger in the reaction mixture, and enhancing reaction rate, selectivity, and yield.
Advances in Carbohydrate Chemistry and Biochemistry by Derek Horton (Eds.)