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A Versatile Route to l-Hexoses:  Synthesis of l-Mannose and l-Altrose

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journal contribution
posted on 12.10.2006, 00:00 authored by Annalisa Guaragna, Carmela Napolitano, Daniele D'Alonzo, Silvana Pedatella, Giovanni Palumbo
An efficient route for the synthesis of orthogonally protected l-sugars has been opened up, starting from the heterocyclic homologating agent 1 and 2,3-O-isopropylidene-l-glyceraldehyde (2). Our synthetic path enables the synthesis of a 2,3-unsaturated-l-pyranoside, which can be suitably functionalized to afford the desired l-hexoses. In this paper, we report the synthesis of l-manno- and l-altro-pyranosides. Moreover, this strategy may be used to prepare all eight sugars and their derivatives in either enantiomeric form.

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