Fluorine-containing carbohydrates

Not surprisingly, one of the most common reactions of pyrrolo[2,3- ]pyrimidines is nucleoside formation. Typical of the process is the reaction of 5 with the fluorine-containing carbohydrate moiety 6 to produce the nucleoside 7 (Scheme 1) <1995JME3957>. Numerous other reports are described in the literature but the number is too large to be cited here. 

The same sequence of diastereoselective reduction of a /i-oxo-y-fluoro sulfoxide followed by Pummerer rearrangement and hydrolysis to the aldehyde has been used successfully in the synthesis of fluorine-containing carbohydrates.10... 

Up to date, a lots of fluorinated compounds were synthesized and biologically evaluated. Among these fluorinated compounds, fluorinated sugars have recently attracted more and more attentions from organic and medicinal chemists. It should be noted that just one fluorine-containing carbohydrate derivative has been isolated from... 

K. Dax, V. Grassberger, and A. E. Stiitz, Simple synthesis of l,5,6-trideoxy-l,5-imino-D-glucitol, the first fluorine-containing derivative of glucosidase inhibitor 1-deoxynojirimycin, J. Carbohydr. Chem., 9 (1990) 903-908. 

Glasser, W. G., U. Becker, and J. G. Todd. 2000. Novel cellulose derivatives. VI. Preparation and diermal analysis of two novel cellulose esters with fluorine-containing substituents. Carbohydrate Polymers 42,393-400. 

Synthesis and Biological Activities of Compounds Containing Fluorinated Carbohydrates. 186... 

The number of naturally occurring, organic fluorine compounds is very small indeed. Compound 1 is1 a nucleoside antibiotic that contains fluorine attached to the carbohydrate ring, replacing H-4 in the D-ribosyl moiety. The presence of fluorine was shown by -n.m.r.-, 19F-n.m.r.-, and mass-spectral data, and the structure of this compound has been confirmed by independent synthesis.9,10... 

In a series of papers, Kent and coworkers reported on the synthesis of the racemic 2-fluorotetritols and 2-fluoropentitols, and related carbohydrates from simple, non-carbohydrate precursors containing a fluorine atom in the carbon chain. Thus, synthesis of 2-deoxy-2-fluoro-DL-erythritol (537) and its threo isomer (538) was accomplished303 by vigorous reduction of ethyl ethoxalylfluoroacetate (536) with lithium... 

Although the major portion of this review is concerned with the glycosyl fluorides and their derivatives, short Sections on the closely related glycosyl azides and on carbohydrates containing fluorine at non-glycosidic carbon atoms have been included. 

The succeeding volume of the series contains reviews on H.p.l.c. of carbohydrates, n.m.r. of fluorinated monosaccharides, the use of photosensitive protecting groups in carbohydrate synthesis and high-temperature transformations of monosaccharides in aqueous solution. ... 

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