
TY  - JOUR
A1  - McAuliffe, Joseph C. 
A1  - Stick, Robert V. 
T1  - &#946;-Acarbose. V. The Synthesis of a Hydroxylated Derivative of a Diastereoisomer of Methyl Acarviosin
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1997
VL  - 50
IS  - 3
SP  - 219
EP  - 224
KW  - 
UR  - https://doi.org/10.1071/C96155 
N2  - 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. 
ER  -

