Collection of Czechoslovak Chemical Communications p. 1665 - 1681 (2001)
Update date:2022-08-04
Topics:
Kefurt, Karel
Moravcova, Jitka
Bambasova, Sarka
Buchalova, Katerina
Vymetalikova, Barbora
Kefurtova, Zdenka
Stanek, Jan
Paleta, Oldrich
1,2-O-Isopropylidene-3-O-methyl-α-D-xylofuranose (2), 1,2-O-isopropylidene-α-D-xylofuranose (3), 2,4-O-ethylidene-D-erythritol (4) and 1,3-O-ethylidene-D-threitol (5) were alkylated with racemic (2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptyl)oxirane (1) using boron trifluoride diethyl etherate as a catalyst. The desired mono- or disubstituted polyfluoroalkyl derivatives 6-11 were isolated only in low to medium yields. The fluoroalkylation was accompanied with disproportional distributions of the protecting acetal/ketal groups and polymerization of saccharides. Therefore the stability of 3, 4, 5, 5-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose (14) and 1,2-O-isopropylidene-α-D-glucofuranose (15) in the presence of a catalytic amount of boron trifluoride diethyl etherate was investigated in various solvents. A mechanism explaining the effect of the catalyst has been proposed.
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Doi:10.1016/S1381-1169(01)00200-X
(2001)Doi:10.1021/om050291q
(2005)Doi:10.1016/j.tet.2008.06.079
(2008)Doi:10.1016/j.bmcl.2012.11.071
(2013)Doi:10.1021/ja053368a
(2005)Doi:10.1021/jo00165a019
(1983)