15430-94-1Relevant academic research and scientific papers
Enantiomerically Pure, Highly Functionalized Tetrahydrofurans from Simple Carbohydrate Precursors
Lundt, Inge,Frank, Holger
, p. 13285 - 13298 (2007/10/02)
6-Bromo-6-deoxy-1,4-aldonolactones and 6-bromo-6-deoxy-alditols with D-galacto, D-altro-, D-manno- and D-ido-configuration were selectively converted into hydroxylated tetrahydrofuran derivatives by simple heating in water.The 6-bromo-6-deoxy-altritol (10) and 6-bromo-6-deoxy-D-iditol (25) reacted even at room temperature.Likewise, 6-bromo-2,6-dideoxy-aldonolactones with D-arabino- (29) and D-lyxo-configuration (31) gave the corresponding 2-deoxy-3,6-anhydride, when heated in water.The rate of formation of the furan ring by intramolecular nucleophilic substitution was determined by the conformation of the bromopolyols in water.
THE CHEMICAL-TRANSFORMATION PRODUCTS OF 1,6-DIBROMO-1,6-DIDEOXYGALACTITOL AND 1,2:5,6-DIANHYDROGALACTITOL IN AQUEOUS SOLUTION
Vidra, Ildiko,Simon, Kalman,Institoris, Laszlo,Csoeregh, Ingeborg,Czugler, Matyas
, p. 41 - 58 (2007/10/02)
After hydrolysis of 1,6-dibromo-1,6-dideoxygalactitol (1) and 1,2:5,6-dianhydrogalactitol (2), 11 compounds were isolated, three of them as tritylated derivatives.Their structures were established on the basis of chemical evidence and, for four compounds, by X-ray diffraction.The main product of the hydrolysis of 1 was 3,6-anhydro-1-bromo-1-deoxy-DL-galactitol; the end-products of the hydrolysis of 2 were 1,5-anhydro-DL-galactitol, 2,5-anhydro-DL-altriol and galactiotol.
