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Stereoconvergent synthesis of 1-deoxynojirimycin isomers by using the 3 component 4 centred Ugi reaction†
Chandra S. Azad,Anil K. Saxena
Organic Chemistry Frontiers Pub Date : 02/16/2015 00:00:00 , DOI:10.1039/C5QO00019J
Abstract

A new reductive cyclization/Ugi multicomponent reaction sequence for the synthesis of 1-deoxyallonojirimycin and 1-deoxyaltronojirimycin has been developed. The method was successfully applied to the azido-hemiacetal derived from commercially available D-ribose. The very selective reagents were used for the synthesis of Ugi bis-amides which were sub sequentially hydrolysed to iminosugars.

Graphical abstract: Stereoconvergent synthesis of 1-deoxynojirimycin isomers by using the 3 component 4 centred Ugi reaction
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