
%0 Journal Article
%A Hayman, Colin M. 
%A Larsen, David S. 
%A Brooker, Sally 
%T A Facile Synthesis of 2,6-Dideoxy 6,6,6-Trifluorinated Carbohydrate Analogues
%J Australian Journal of Chemistry
%D 1998/07/13
%V 51
%N 7
%P 545-554
%K 
%R https://doi.org/10.1071/C97203
%U https://www.publish.csiro.au/paper/C97203 
%X The syntheses of 2,6-dideoxy-6,6,6-trifluoro-DL-arabino-hexose (4) and the corresponding glycoside, ethyl 2,6-dideoxy-6,6,6-trifluoro-DL-arabino-hexopyranoside (11), are described. The key step in the synthesis of (4) involved the Lewis acid catalysed hetero-Diels&#8211;Alder reactions of (E)-4-benzyloxy-1,1,1-trifluorobut-3-en-2-one and benzyl vinyl ether. Hydroboration of the resulting cycloadduct, and hydrogenylitic debenzylation gave (4) in a 59% overall yield. The ethyl glycoside (11) was prepared in a similar manner from ethyl vinyl ether. A single-crystal X-ray diffraction study confirmed the structural assignment of (11). The O-glycosides (17) and (18) were formed from the boron trifluoride etherate promoted reaction of the per-acetate of (4), i.e. (16), and 2-naphthol. However, a similar reaction between 5-hydroxy-1,4-dimethoxynaphthalene and (16) gave the disubstituted C-glycoside (19) in 52% yield. 
