Carbohydrates glycosyl compounds

The anion of nitromethane adds easily to the carbonyl functions of sugars. This is a useful strategy for extension of the carbon chain.100 2-Acetamido-2-deoxy-P-D-glucose (A-acetyl-D-glucosamine) is the carbohydrate unit of glycoproteins that occurs most often. The nitromethy-lation method provides a straightforward route to a series of C-glycosyl compounds with the acetamido functionality (Eq. 3.62).101... 

The term glycal is used to define sugar derivatives having a double bond between C-1 and C-2. Accordingly, C-1 glycals are A1,2 unsaturated carbohydrate derivatives with a carbon substituent at the anomeric position. These compounds are versatile synthetic intermediates, owing to the variety of transformations associated with their enol ether functionality, and have found ample use in the preparation of C-glycosyl compounds,1 carbohydrate mimics,2 and natural products.3... 

Glycosuloses, 3-deoxy-, and the degradation of carbohydrates, 19, 181-218 Glycosylamines, 10, 95-168 Glycosyl azides, 16, 85-103 C-Glycosyl compounds, naturally occurring, 18, 227-258 20, 357-369 Glycosyl esters,... 

Bertozzi, C, Bednarski, M, C-glycosyl compounds bind to receptors on the surface of Escherichia coli and can target proteins to the organism, Carbohydr. Res., 223, 243-253, 1992. 

BeUosta, V, Czemecki, S, C-glycosyl compounds. Part X. Reaction of organocuprate reagents with protected 1,2-anhydro sugars. Stereocontrolled s3mthesis of 2-deoxy-C-glycosyl compounds, Carbohydr. Res., 244, 275 -284, 1993. 

Orsini, F, Pelizzoni, F, Synthesis of C-glycosyl compounds the reaction of acetylated glycals with fert-hutoxycarhonylmethylzinc bromide, Carbohydr. Res., 243, 183-189, 1993. 

Kozikowski, A P, Konoike, T, Ritter, A, OrganometaUics in organic synthesis. Applications of a new diorganozinc reaction to the synthesis of C-glycosyl compounds with evidence for an oxonium-ion mechanism, Carbohydr. Res., 171, 109-124, 1987. 

Ichikawa, Y, Isobe, M, Konobe, M, Goto, T, S3mthesis of C-glycosyl compounds from 3,4,6-tri-O-acetyl-l,5-anhydro-D-arabino-hex-l-enitol and allyltrimethylsilane and bis(trimethylsilyl)acetylene, Carbohydr. Res., 171, 193-199, 1987. 

Bellosta, V, Chassagnard, C, Czernecki, S, C-glycosyl compounds. Part VIII. Stmctural studies by proton and carbon-13 NMR spectroscopy and circular dichroism of acetylated a- and 3-D-gluco-and -manno-pyranosylarenes, Carbohydr. Res., 219, 1-7, 1991. 

Kunz, H, Muller, B, Weissmuller, J, Stereoselective synthesis of C-glycosyl compounds via Michael addition of trimethylsilyl enol ethers and enamines to hex-l-enopyran-3-uloses, Carbohydr. Res., 171, 25-34, 1987. 

Dheilly, L, Frechou, C, Beaupere, D, Uzan, R, Demailly, G, A new route to C-glycosyl compounds. Wittig-type reaction promoted hy zinc, Carbohydr. Res., 224, 301-306, 1992. 

Sun, K M, Dawe, R D, Fraser-Reid, B, Synthesis and anomerization of C-glycosyl compounds related to some heteroxyxlic natural products, Carbohydr. Res., 171, 35 -47, 1987. 

Wilcox, C S, Cowart, M D, New approaches to synthetic receptors. Studies on the synthesis and properties of macrocyclic C-glycosyl compounds as chiral, water-soluhle cyclophanes, Carbohydr. Res., 171, 141-159, 1987. 

Bellosta, V, Czernecki, S, C-glycosyl compounds. IV. Synthesis of (2-deoxy-a-D-glyc-2-enopyr-anosyl)arenes by stereospecific conjugate addition of organocopper reagents to peracetylated hex-1-enopyran-3-uloses, Carbohydr. Res., 171, 279-288, 1987. 

Brakta, M, Lhoste, P, Sinou, D, Banoub, J, Functionalized C-glycosyl compounds. Part II. Synthesis of the anomeric ethyl 2-(4,6-di-0-benzyl-2,3-dideoxy-D-erythro-hex-2-enopyranosyl) acetates and their structural characterization, Carbohydr. Res., 203, 148-155, 1990. 

Grindley, T B, Wickramage, C, A novel approach to the synthesis of C-glycosyl compounds the Wittig rearrangement, J. Carbohydr. Chem., 1, 661-685, 1988. 

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