Sugars deoxy, properties

The deoxyinositols (quercitols, cyclohexanepentols) are useful model compounds which display many of the physical and chemical properties of true deoxy sugars. Although (-b)-proto-quercitol, the best known isomer, was isolated from nature 118 years ago, no synthesis has been reported up until now. The synthesis here described is actually that of the (-)-enantiomer, starting with (-)-inositol however, identical procedures applied to the readily available ( + ) or dl-inositol would give (- -) or DL-proto-quercitol, respectively. The natural occurence of, )-proto-quercitol has... 

Deoxy-sugars. Part IX. Some Properties and Reactions of 2-Deoxy-D-galactose, W. G. Overend, F. Shafizadeh, and M. Stacey,/. Chem. Soc., (1950) 671 -677. 

Amino-sugars and Related Compounds. Part VIII. Some Properties of 2-Deoxy-2-sulphoamino-D-glucose, Heparin, and Related Substances, A. B. Foster, E. F. Martlew, M. Stacey, P. J. M. Taylor, and J. M. Webber, /. Chem. Soc., (1961) 1204-1208. 

Amide derivatives have proved especially useful sugars for study by c.d. spectroscopy. The amide substituent is the same as the chromophore found in proteins, so that its optical properties have been extensively studied both experimentally and theoretically. 2-Acetamido sugars are found in many glycoproteins. The structure of 2-acetamido-2-deoxy-a-D-glucopyranose is given as an example in formula 7. 

The taste properties of the di-O-methylhexopyranosyl derivatives, like those of the corresponding deoxy sugars, are never sweet, and always bitter. As with the deoxy sugars, this is possibly the result of increased lipophilicity of the molecule. In sucrose, however, the presence of two methyl groups on the D-glucopyranosyl or the D-fructofuranosyl group does not seem to cause any marked bitterness (see Table XVIII). 

R. F. Butterworth and S. Hanessian, Tables of the properties of deoxy sugars and their simple derivatives, Adv. Carbohydr. Chem. Biochem. 26 279 (1971). 

---