190784-97-5Relevant academic research and scientific papers
An investigation into the synthesis of some molecules related to methyl acarviosin
McDonough, Matthew J.,Stick, Robert V.,Tilbrook, D. Matthew G.,Watts, Andrew G.
, p. 233 - 241 (2007/10/03)
Methyl acarviosin is an impressive inhibitor of some glycoside hydrolases that process substrates containing α-D-glucosidic linkages. In an attempt to provide putative inhibitors for enzymes that process β-D-glucosidic linkages, we report an improved synthesis of a hydroxylated 'methyl β-acarviosin' and our efforts towards various deoxygenated versions of methyl β-acarviosin. As well, the synthesis of a 1,3-linked variant of methyl β-acarviosin is reported, together with an unsuccessful 'tether' approach to construct the crucial nitrogen linkage in the acarviosins.
β-acarbose. V * the synthesis of a hydroxylated derivative of a diastereoisomer of methyl acarviosin
McAuliffe, Joseph C.,Stick, Robert V.
, p. 219 - 224 (2007/10/03)
The treatment of a 1-epivalienamine derivative with 1,6:3,4-dianhydro-2-O-benzyl-β-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 β-D-glucoside and base hydrolysis provided the 6-hydroxylated derivative of a diastereoisomer of methyl acarviosin, a putative inhibitor of enzymes which process β-D-glucosidic linkages.
