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Stereoselective synthesis of t-butyl 2-amino-2,5-dideoxy- - -pentanoate: Formal synthesis of l-daunosamine

1987; Elsevier BV; Volume: 43; Issue: 10 Linguagem: Inglês

10.1016/s0040-4020(01)86816-2

1464-5416

Luca Banfi, Silvia Cardani, Donatella Potenza, Carlo Scolastico,

Chemical Synthesis and Analysis

Enantiomerically pure t-Butyl 2-amino-2,5-dideoxy-L-lyxo-pentanoate 4c is synthesized via the highly diastereoselective MgBr2 mediated addition of dibenzylamino acetate silylketene acetal 2 to O-benzyl lactic aldehyde 3. The synthesis of γ-lactone 5c, a known intermediate in the synthesis of L-daunosamine and L-vancosamine, is also described.