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 via learn experts that combine commercial, analytical, and technological features of biochemistry, natural chemistry, and instrumentation method within the research of carbohydrates.Contributions from prime gurus and specialists Informs and updates on all of the most modern advancements within the box

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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.

Olivoses (2,6-dideoxy-D- and -L-arabino-hexoses) are components often present in bioactive glycosylated natural products, particularly in antitumor antibiotics of the aureolic acid family, some of which are used clinically. 71 employed montmorillonite K-10 as catalyst for the glycosidation of 3,4-di-O-protected olivoses (30–34) with alcohols (35–40) (Scheme 7). 3/1). The nature of the protecting groups in the olivose was recognized as being essential for the stereochemical outcome of the glycosidation.

Ferrier rearrangement catalyzed by acid zeolites. 48 This transformation involves migration of the glycal double bond with loss of an acyloxy group at the allylic position, under catalysis by Lewis acids. The intermediate delocalized carbenium ion then reacts with O-, C-, N-, or S-nucleophiles to give the corresponding 2,3-unsaturated glycosyl derivatives. Various catalysts have been used in this reaction, boron trifluoride etherate being the Lewis acid most frequently employed. Ferrier rearrangement of glycals possessing ether protection at the allylic position has only been reported for 3-Omethyl-D-glucal49 and 3-O-benzyl-D-glucal,50 under catalysis by boron trifluoride etherate.

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