A stereoselective transformation of (−)-shikimic acid into (3R,4S,5R,7R)-7-(hydroxymethyl)azepane-3,4,5-triol, a potential glycosidase inhibitor

Add time:09/24/2019    Source:sciencedirect.com

A stereoselective synthesis of (3R,4S,5R,7R)-7-(hydroxymethyl)azepane-3,4,5-triol hydrochloride from (−)-shikimic acid is described. The method involves the transformation of (−)-shikimic acid into (4S,5R)-2,2-dimethyl-5-((R)-1′,4′-di(tert-butyldimethylsilyl)oxy-3′-oxobutyl)-1,3-dioxolane-4-carbaldehyde 9b, followed by a double reductive amination of this dicarbonyl compound to the final product.

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