Abstract:An efficient stereoselective synthesis of L-imino-C-gulosides is disclosed. Starting from the 2,3:4,6-di-O-isopropylidene-Dmannopyranose the synthetic pathway involves first a Wittig reaction with CMPP to introduce the carbon at the pseudo-anomeric position, followed by a Michael reaction under ultrasound activation to introduce the nitrogen center, and finally a Mitsunobu reaction for the ring closure leading to the C-iminosugar from the L-series.Among carbohydrate mimetics, iminosugars (or azasugars), in whi… Show more
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