Carbohydrate-derived spiroketals: stereoselective synthesis of di-D-fructose dianhydrides via intramolecular aglycon delivery.
[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.
Rubio
Enrique M
EM
Instituto de Investigaciones Químicas, CSIC, Américo Vespucio s/n, Isla de la Cartuja, E-41092 Sevilla, Spain.
Ortiz Mellet
Carmen
C
García Fernández
José M
JM
D003500:Cyclization; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D005632:Fructose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D004988:Ethers, Cyclic; D007202:Indicators and Reagents; D013141:Spiro Compounds; D005632:Fructose