Ribofuranose properties

The conformational properties of furanose rings have received considerable attention in recent years because of the impact these properties may have in mediating biological processes . Most notable in this respect are the p-D-ribofuranose 1 and 2-deoxy-p-D-erythro-pentose 2 (Scheme 1) components of ribo- (RNA) and deoxyribonucleic (DNA) acids. It is well known that the furanose ring adopts specific shapes depending on its local structural environment in a biopolymer. For example, in tRNA, the... 

Trimethyl-D ribofuranose, having the same properties, has since been synthesized by Levene and Stiller. ... 

The dienophilic properties of vinylene carbonate (1,3-dioxol-2-one, 6) have been repeatedly exploited for the synthesis of cyclic polyols. Recently a number of ribofuranose derivatives have been synthesized starting from 6. The known adduct 7, obtained from 6 and furan, was c/r-hydroxylated, and after acetonation was hydrolyzed with base and cleaved with permanganate to give the dicarboxylic acid 8. The corresponding anhydride 9 gave, on treatment with trimethylsilyl azide, the isocyanate 10, which in turn was converted into the carbonate 11 on addition of methanol. The monoester 12, obtained in the reaction of anhydride 9 with isopropanol, was effectively resolved into enantiomers by the use of brucine or (/ )-l-(2-naphthyl)ethylamine. ... 

Ness, R. K., and H. G. Fletcher, Jr. 2-Deoxy-D-er> f/iro-pentose. X. Synthesis of l,4-Anhydro-3,5-di-0-benzoyl-2-deoxy-D-er> //iro-pentose-l-enol. Derivatives of a Furanose-related Glycal. J. Organ. Chem. (U.S.A.) 28, 435 (1963) Haga, M., and R. K. Ness Preparation and Properties of 3,5-Di-0-p-anisoyl-l,2-dideoxy-D-er> t/iro-pentofuranose-l-ene. Various p-Anisoylated Derivatives of D-Ribofuranose. J. Organ. Chem. (U. S. A.) 30, 158 (1965). 

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