
TY  - JOUR
A1  - Best, Wayne M. 
A1  - Ferro, Vito 
A1  - Harle, Julia 
A1  - Stick, Robert V. 
A1  - Tilbrook, D. Matthew G. 
T1  - The Synthesis of Some Epoxyalkyl <font face = "symbol">b</font>-<emph type="2">C</emph>-Glycosides as Potential Inhibitors of <font face = "symbol">b</font>-Glucan Hydrolases
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1997
VL  - 50
IS  - 5
SP  - 463
EP  - 472
KW  - 
UR  - https://doi.org/10.1071/C97015 
N2  - The treatment of tetra-O-benzyl-D-glucono-1,5-lactone with various alkenylmagnesium halides gave the intermediate lactols which, upon reduction (Et3SiH/BF3) and protecting group manipulation, yielded alkenyl tetra-O-acetyl-&#946;-D-C-glucopyranosides in good yield. These &#946;-D-C-glucosides were precursors of the epoxyalkyl &#946;-D-C-glucopyranosides, themselves putative inhibitors of b-glucan hydrolases. Similar additions of Grignard reagents to per-benzylated cellobionolactone were not as successful in yielding epoxyalkyl &#946;-C-cellobiosides. The addition of Grignard reagents to 1,2-anhydro-3,4,6-tri-O-benzyl-&#945;-D- glucose offers a viable alternative route to the prop-2-enyl &#946;-D-C-glucoside, but not to the but-3-enyl and pent-4-enyl counterparts. Likewise, the addition of Grignard reagents to a 1,2-anhydro cellobiose gave disappointing results. Preliminary results are reported for a novel approach to alkenyl &#946;-D-C-glucosides by the alkylation of nitromethyl &#946;-D-C-glucosides. 
ER  -

