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We have synthesized imino sugar scaffolds bearing two points of diversity -the stereocenters located in α positions relative to the nitrogen atom -and three points of orthogonal derivatization -a carboxylic function, the primary hydroxy group, and the ring nitrogen atom. The key steps in the synthetic approach are the chain elongation of aldehyde 5 with the formation of an α,β-unsaturated ester, the Michael addition of an amine, and the final cyclization. This strategy leads to the preparation of different N-substituted imino

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Synthesis of the Dimethyl Ester of 1-Deoxy-L-idonojirimycin-1-methylenephosphonate: A New Approach to Iminosugar Phosphonates. -Title compound (VIII) is prepared starting from commercially available tetrabenzyl glucose (I). Key steps are the substitution of the hydroxyl group at C-5 of (II) by an azido group, the stereoselective reaction of the aldehyde (IV) with (V), the conversion of the azido into an amino group and finally the cyclization of (VI) to (VII). -(LA FERLA*, B.; BUGADA, P.; NICOTRA, F.; J. Carbohydr. Chem. 25 (2006) 1-3, 151-162; Dip. Biotecnol. Biosci., Univ. Stud. Milano, I-20126 Milano, Italy; Eng.) -M. Bohle 48-196