
%0 Journal Article
%A McAuliffe, Joseph C. 
%A Stick, Robert V. 
%T &#946;-Acarbose. V. The Synthesis of a Hydroxylated Derivative of a Diastereoisomer of Methyl Acarviosin
%J Australian Journal of Chemistry
%D 1997/05/05
%V 50
%N 3
%P 219-224
%K 
%R https://doi.org/10.1071/C96155
%U https://www.publish.csiro.au/paper/C96155 
%X The treatment of a 1-epivalienamine derivative with 1,6:3,4-dianhydro-2-O-benzyl-&#946;-D-galactose has given an amino alcohol capable of conversion into either a cyclic carbamate or an aziridine. All attempts at acetolysis of the 1,6-anhydro ring of the cyclic carbamate failed owing to the inherent reactivity of the (allylic) benzyl ethers present in the molecule. Therefore, following a reduction with lithium in ammonia and acetylation of the product, a new cyclic carbamate was obtained which underwent successful acetolysis to provide a heptaacetate. This heptaacetate could be transformed into the desired methyl &#946;-D-glucoside and base hydrolysis provided the 6-hydroxylated derivative of a diastereoisomer of methyl acarviosin, a putative inhibitor of enzymes which process &#946;-D-glucosidic linkages. 
