129870-01-5Relevant articles and documents
Regioselective opening of epoxyaldonolactones to fluorodeoxyaldonolactones using tetrabutylammonium dihydrogentrifluoride
Lundt,Albanese,Landini,Penso
, p. 7295 - 7300 (1993)
A study on the hydrofluorination of epoxyaldonolactones with Bu4N+H2F3- (1) under solid-liquid PTC and homogeneous conditions has been performed. Unsubstituted 5,6-epoxy-hexono-1,4-lactones 2a give the corresponding fluorohydrins in high yield using catalytic amounts of 1 and an excess of solid KHF2, while an equimolar amount of 1 is used with 2,3-epoxyaldonolactones 2d-g and 5,6-epoxy-hexono-1,4-lactones containing a free hydroxy group 2b,c. In all cases the reaction is completely regio- and stereoselective affording 6-deoxy-6-fluoro-hexonolactones 3a,b and 2-deoxy-2-fluoro-aldonolactones 3d,f.
Preparation of 2,3-Epoxyaldonolactones and their Conversion into 2-Fluoro-2-deoxy-aldonolactones and -sugars
Bols, Mikael,Lundt, Inge
, p. 252 - 256 (2007/10/02)
Treatment of the 2-bromo-2-deoxylactones 1, 2 and 8 with potassium fluoride in acetonitrile or acetone gives the corresponding 2,3-epoxylactones 4,5 and 10, respectively.The γ-lactones 5 and 10 were in equilibrium with the corresponding δ-lactones 7 and 12.The 2,5-dibromo-2,5-dideoxypentonolactones 3 and 9 gave the 2,3-epoxylactones 6 and 11, respectively, when treated with potassium carbonate in acetone.By treatment of the 2,3-epoxylactones with Et3N*3HF at 70 deg C for 3-13 days the 2-fluoro-2-deoxylactones 13, 15 and 18 were obtained in 57-69 percent yield; 15 and 18 were converted into 2-fluoro-2-deoxy-D-xylose (17) and -D-arabinose (19), respectively.Hydrolysis of 13 gave crystalline 2-fluoro-2-deoxy-L-threonic acid.