132016-21-8

Upstream product

• 176389-14-3 (1S,2S,3S,4R,5R)-4-Benzyloxy-2-((1R,4R,5S,6S)-4,5,6-tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enylamino)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol 
• 128573-02-4 (1R,2S,3S,4R)-1-amino-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-2,3,4-triol 
• 132016-22-9 (1S,2R,9S,10S)-9-amino-4,4,12,12-tetramethyl-3,5,11,13-tetraoxatricyclo[8.3.0.0^2,7]tridec-7-ene 
• 33159-54-5 2-O-acetyl-1,6:3,4-dianhydro-β-D-galactopyranose 
• 33208-46-7 1,6:3,4-Dianhydro-2-O-benzyl-β-D-galactopyranose 

Relevant academic research and scientific papers

β-acarbose. V * the synthesis of a hydroxylated derivative of a diastereoisomer of methyl acarviosin

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.