By R. J. Ferrier
Carbohydrate Chemistry presents evaluation insurance of all guides correct to the chemistry of monosaccharides and oligosaccharides in a given 12 months. the quantity of analysis during this box showing within the natural chemical literature is expanding end result of the more suitable significance of the topic, particularly in parts of medicinal chemistry and biology. In no a part of the sector is that this extra obvious than within the synthesis of oligosaccharides required by means of scientists operating in glycobiology. Clycomedicinal chemistry and its reliance on carbohydrate synthesis is now rather well tested, for instance, through the training of particular carbohydrate- established antigens, specially cancer-specific oligosaccharides and glycoconjugates. insurance of issues similar to nucleosides, amino-sugars, alditols and cyclitols additionally covers a lot study of relevance to organic and medicinal chemistry. each one quantity of the sequence brings jointly references to all released paintings in given parts of the topic and serves as a complete database for the energetic study chemist. expert Periodical reviews supply systematic and particular assessment assurance in significant components of chemical examine. Compiled through groups of major gurus within the suitable topic components, the sequence creates a different carrier for the energetic study chemist, with common, in-depth bills of growth particularly fields of chemistry. topic assurance inside diversified volumes of a given identify is the same and e-book is on an annual or biennial foundation.
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Additional info for Carbohydrate Chemistry v.25
Example text
Chem. , 1987, 1009) on the preparation of vinyl and 1' -substituted vinyl glycosides (6) from tetra-0-acetyl-a-D-glucopyranosyl bromide (5) and bis(acylmethy1)mercury reagents has appeared. The 2,3-unsaturated phenylthioglycoside (7), with these reagents, similarly gives 2,3-unsaturated products (8) which rearrange to C-glycosides (9 ) on zinc bromide treatment and to C-3-branched glycals (10) on heating (Scheme idr.. H , Me,P h AcO CH~OAC (5) OL AcO - CH20Ac &O OAc L ' iii, A S c h e m e lo Glycosides of amino-sugars remain of importance, see Chapter 9, where reference is made to the use of 2-trifluoroacetamido-2-deoxy-p-D-galactopyranosyl fluoride as a glycosylating agent.
S . Nishibori, and S. KawaLishi, Agric. Biol. 55. 1159. G. Braca. R. Galletti, and G. Sbrana,J . Orgunomet. Abstr.. 115. 232 685). N. Greenspoon, and E. Wachtel, J. Am. Chem. , 1991,113,7233. R. Ostaszewski, U. Jacobson. and J. Jmzak. Bull. Pol. Acud. 347 (Chem. Absfr.. 1991. 114, 6472). K. Tanaka, T. Takeda. and K. Phurm. , 1991,39. 1091. ' The same group have reported on the synthesis and use of 1-0-pent-4-enoylglycosesin glycosidations. ' Mukaiyama's group have shown that use of 1-0-acetyl-2,3,4,6-tetra-O-benzyl-D-glucose and trimethylsilylated alcohols in the presence of Lewis acid catalysts leads to high yields of glycosides with remarkably high a$ ratios (9:l or better).
A report of the decylization of hexa-0-acetyl-D-gentiobal synthesis of several carbo-glucose-based disaccharides is referred to in Chapter 18. 36 Carbohydrate Chemistry In the area of D-galactosyl disaccharides, transferase enzymes have been studied by several groups. lW The E. coli enzyme has been immobilized on cellulose beads. 133 Several sulfates of lactose are referred to in Chapter 7. The amino-disaccharide (86) was made by a displacement of a triflyloxy group from a derivative of the corresponding galactosyl glucosamine,” and the lactose based 2-oximinoglycosyl chloride (87) has been used as the starting material to produce 0-linked serine glycosides with the u-gluco- and p-rnanno- configurations and the 2-acetamido-2-deoxy analogues.