Dicarbonyl sugars

Derivatives of 6-deoxy-hex-5-enopyranosides are important intermediates in the synthesis of dicarbonyl sugars, namely hexos-5-uloses. For... 

Streptose is the first branched-chain sugar to have been identified as a component of a biological compound produced by a microorganism. This dicarbonyl sugar is known only in its derivatives. The chemistry of streptose and streptomycin has been lucidly reviewed by Lemieux and Wolfrom.1 In this article, it was noted that streptose must be either 5-deoxy-3-C -formyl-L-ribose or 5-deoxy-3-C-formyl-L-lyxose. Since then, the presence of the latter configuration (XXXIV) has been definitely established by Wolfrom and DeWalt,66 who found that N-acetyltetrahydrostreptobi-... 

The tautomerism of 1-nitroprop-l-enyl sugars into a,p-unsaturated oximes is catalysed by potassium fluoride in the presence of tetra-n-butylammonium hydrogensulphate, providing a route to 1,3-dicarbonyl sugar derivatives [7],... 

Miksik, I., Gabriel, J., Deyl, Z. (1997). Microemulsion electrokinetic chromatography of diphenylhydrazones of dicarbonyl sugars. J. Chromatogr. A 772 297-303. 

This "doubly glycosidic anellation of - formally - a 2,3-diketosugar onto a diol is highly reminiscent structurally of the broad spectrum antibiotic spectinomycin (41) and the cardiac glycosides isolable from the latex and leaves of Calotropis procera (42) a bushy plant indigenious in wide parts of Africa and India. In these, a pyranoid 4-deoxy-2,3-dicarbonyl sugar, which has been... 

M. S. Feather, Dicarbonyl sugar derivatives and their role in the Maillard reaction, in Thermally Generated Flavors Maillard, Microwave, and Extrusion Processes, T. H. Parliment, M. J. Morello, and R. J. McGorrin (eds), American Chemical Society, Washington, DC, 1994, 127-141. 

Dicarbonyl sugars, III, 103 Dichroism of flow, of starch-iodine complex of A fraction, I, 266 Diffusion constants, of starch acetates, I, 295... 

Similar suffixes can be constructed for dicarbonyl sugars and other modifications, for example ... 

An increasingly employed version of Approach A, the condensation of a dicarbonyl sugar with ammonia or a suitable amine, was, amongst others, reported by Reitz and Baxter [166] and is based on double reductive amination of glucose-derived 5-ulose 66 (Scheme 9.8). 

Baxter, E W, Reitz, A B, Expeditious synthesis of azasugars by the double reductive amination of dicarbonyl sugars, J. Org. Chem., 59, 3175-3185, 1994. 

A considerable contribution to oin knowledge of the chemistry of dicarbonyl sugars, a group of sensitive and reactive compounds, has been made by Theander, who used, for the most part, acetals of D-glucose, D-mannose, and n-galactose. Carbonyl derivatives of aldoses and aldosides are of importance in the synthesis of branched-chain sugars. ... 

The synthesis of cyclitols from 5-dicarbonyl sugars has been reviewed. ... 

Dicarbonyl sugars glycos-2-uloses — Dicarbonyl sugars glycos-2-uloses... 

Dicarbonyl sugars glycos-3-uloses - Dicarbonyl sugars glycos-4-uloses... 

Dicarbonyl sugars glycos-S-uloses - Aldonic acids and lactones... 

Hirsch, J., Petrakova, A., and Feather, M. S., 1992, The reaction of some dicarbonyl sugars with aminoguanidine, Carbohydr. Res. 232 125-130. 

Methods have been described for the purification and h.p.l.c. analysis of 3-deoxy-D-eO r/iro-hexos-2-ulose. Its reactivities in acid and base have also been studied. Anotho- method for the detection of this aldosulose in plasma and urine is mentioned in C3iapter 23. Sucrose and isomaltulose have been oxidised using Agrobacterium tumefaciens to their 3-keto derivatives. The reaction of dicarbonyl sugars with aminoguanidine is discussed in Chapter 10, and the synthesis of the antibiotic cortalcerone is covered in Chapter 19. 

Substituted thiazoles, which on deprotection afford aldehydes, have been utilized in the synthesis of derivatives of dicarbonyl sugars such as the methyl glycoside 3. Various procedures for the selective oxidation of both protected and unprotected glycals at the aUylic position are discussed in Chapter 13. The pyrone 4 and the diketone dihydrate 5 have been... 

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