507239-27-2

Upstream product

• 507238-66-6 (3R,4S)-3,4-dibenzyloxy-5-(benzyloxymethyl)-5-[(tert-butyl)dimethylsilyloxy]deca-1,9-diene 
• 507238-34-8 (3R,4S)-3,4-dibenzyloxy-5-(benzyloxymethyl)deca-1,9-dien-5-ol 
• 220939-94-6 (3S,4R)-1,3,4-tris(benzyloxy)-hex-5-en-2-one 

Relevant academic research and scientific papers

Synthesis of seven- and eight-membered carbasugar analogs via ring-closing metathesis and their inhibitory activities toward glycosidases

An expeditious and efficient synthesis of new enantiopure polyhydroxylated seven- and eight-membered carbocycles is described starting from 2,3,5-tri-O-benzyl-D-arabinose. The key cyclization step involves ring closing metathesis of 1,8- and 1,9-dienes using Grubbs' catalyst. All of the new carbasugar analogs synthesized were evaluated as glycosidase inhibitors. Contrary to our expectations, (1S,2S,3R,4R,5R)-1-(hydroxymethyl)-cyclohepta-1,2,3,4,5-pentol which has the β-D-mannopyranose configuration for C(1)-C(5) inhibits α- and β-glucosidases, whereas its diepimer (1S,2S,3R,4S,5S)-1-(hydroxymethyl)-cyclohepta-1,2,3,4,5-pentol, which has the α-D-glucopyranose configuration, is not recognised by these enzymes.