Article

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: 6.14). 03/2003; 5(6):873-6. DOI:10.1021/ol034022c
Source: PubMed

ABSTRACT [reaction: see text] A one-pot synthesis of C(2)-symmetric di-d-fructose dianhydrides having the 1,6,9,13-tetraoxadispiro [4.2.4.2]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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