Monosaccharides higher-carbon

For a review, see Jarosz, S, Synthesis of higher carbon sugars via coupling of simple monosaccharides — Wittig, Homer-Emmons, and related methods, J. Carbohydr. Chem., 20, 93-107, 2001. 

Jarosz, S, Salanski, P, Mach, M, Application of stabilized sugar-derived phosphoranes in the synthesis of higher carbon monosaccharides. First synthesis of a C-21-dialdose, Tetrahedron, 54, 2583-2594, 1998. 

In total about 250 different, naturally occurring monosaccharides have been isolated and identified. Interestingly, the monosaccharides produced by nature are almost exclusively in the form of pentoses and hexoses, with the higher carbon sugars (more than nine) rarely occurring in nature. 

Among the higher-carbon monosaccharides, the most important examples are the nine-carbon amino sugar A-acetylneuraminic acid (5-acetamido-3,5-dideoxy-D-g/ycero-a-D-gfl/flcto-non-2-ulopyranosonic acid, Neu5Ac Scheme 11), the parent member of the family of sialic acids, and the eight-carbon sugar... 

A general method for the stereoselective synthesis of monosaccharides from furan compounds [30, 31] has provided a possible route to higher-carbon sugars. 

Enantiomerically pure tetroses, pentoses, and hexoses have been synthesized by the following reaction sequence (A.W.M. Lee, 1982 S.Y. Ko, 1983), which is useful as a repetitive two-carbon hotnologi-.ation in total syntheses of higher monosaccharides and other polyhydroxy compounds (1) Wittig reaction of a protected hydroxy aldehyde with (triphenylphosphor-... 

Of all the monosaccharides d (+) glucose is the best known most important and most abundant Its formation from carbon dioxide water and sunlight is the central theme of photosynthesis Carbohydrate formation by photosynthesis is estimated to be on the order of 10 tons per year a source of stored energy utilized directly or indi rectly by all higher forms of life on the planet Glucose was isolated from raisins m 1747 and by hydrolysis of starch m 1811 Its structure was determined in work culmi nating m 1900 by Emil Fischer... 

L. Hough and A. C. Richardson, The monosaccharides Pentoses, hexoses and higher sugars, in D. J. Coffey, (Ed.), Rodd s Chemistry of Carbon Compounds, Vol. IF, Elsevier, Amsterdam, 1967, pp. 67-595. Chapter 23. 

By means of the cyanohydrin reaction, higher sugars of the heptose. octosc, and nonosc types have been prepared. A monosaccharide such as an aldohexosc may be converted into the next lower monosaccharide, such as an aldopeniosc. by oxidation to the acid, which corresponds to the aldohexose. then treating the calcium salt solution of this acid with a solution or ferrous acetate plus hydrogen peroxide. Carbon dioxide is evolved and aldopentose formed. 

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