Non-chair six-membered-ring conformations. Preference for a twist-boat (or skew) structure in α-L-sorbopyranose derivatives

Add time:09/06/2019    Source:sciencedirect.com

The conformational preferences for 2,3-O-isopropylidene-α-L-sorbopyranose derivatives 3–6 were determined by using 1H NMR data and empirical force field calculations. Proton NMR studies of 3–6 indicate that a twist-boat (or skew) conformation (3S0) prevails over possible chair forms for each compound. Force-field calculations (MM2, MNDO, AM1) on a model 2,3-O-isopropylidene-α-L-sorbopyranose system (18) indicate that the 3S0 conformation is among the low-energy structures. X-Ray crystallographic analysis of α-L-sorbopyranose sulfamate 3, a compound with potent anticonvulsant activity, demonstrates that the 3S0 skew conformation is manifested in the solid state, as well.

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