Carbohydrate-Derived Spiroketals: Stereoselective Synthesis of Di- d -fructose Dianhydrides via Intramolecular Aglycon Delivery

Instituto de Investigaciones Químicas, CSIC, Américo Vespucio s/n, Isla de la Cartuja, E-41092 Sevilla, Spain.
Organic Letters (Impact Factor: 6.36). 03/2003; 5(6):873-6. DOI: 10.1021/ol034022c
Source: PubMed


[reaction: see text] A one-pot synthesis of C(2)-symmetric di-d-fructose dianhydrides having the 1,6,9,13-tetraoxadispiro []tetradecane skeleton has been accomplished via intramolecular aglycon delivery from (6 --> 6) xylylene-tethered fructofuranose precursors. The stereochemical outcome of the glycosylation-spiroketalization process is governed by the geometrical constraints imposed by the rigid tetracyclic structure of the final compound.

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