
TY  - JOUR
A1  - Fairweather, Jon K. 
A1  - McDonough, Matthew J. 
A1  - Stick, Robert V. 
A1  - Tilbrook, D. Matthew G. 
T1  - Some Approaches to Glycosylated Versions of Methyl &#946;-Acarviosin
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2004
VL  - 57
IS  - 3
SP  - 197
EP  - 205
KW  - glycosylation &#8212; trisaccharides &#8212; carbohydrates &#8212; cellulase inhibitors &#8212; hydrolases
UR  - https://doi.org/10.1071/CH03203 
N2  - In a first approach to a glycosylated version of &#8216;methyl &#946;-acarviosin&#8217;, a putative inhibitor of cellulases, cellobiose was converted into a carbocyclic enone that could not be transformed into the required amine for a subsequent alkylation. Alternatively, methyl &#946;-acarviosin itself was glycosylated at C4&#8242;, using a &#8216;glycosynthase&#8217;, to provide the &#8216;trisaccharide&#8217; (and some &#8216;tetrasaccharide&#8217;). Both of these molecules were effective inhibitors of various cellulases. In a related approach to a regioisomer of the above &#8216;trisaccharide&#8217;, a selectively protected derivative of 1-epivalienamine was alkylated with a carbohydrate triflate to give a &#8216;disaccharide&#8217; that could not be glycosylated to give the desired &#8216;trisaccharide&#8217;. Another unsuccessful approach to this molecule is also reported. 
ER  -

