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A novel dioxabicyclo[3.3.1]nonane, a key intermediate in the synthesis of erythronolide B seco-acid
V M Lynch1, W C Lee, S F Martin
1Department of Chemistry and Biochemistry, University of Texas at Austin 78712.
Acta Crystallographica. Section C, Crystal Structure Communications
|September 15, 1994
Abstract:
In the title compound, (1R,4S,5R,6R,8R)-1-ethyl-4,6,8-trimethyl-2,9-dioxabicyclo[3.3.1]++ +nonan-6-yl 1-imidazolecarboxylate, C16H24N2O4, the 2,9-dioxabicyclo[3.3.1]nonane ring system assumes a double-chair conformation. Bond angles around the ring are enlarged compared to normal tetrahedral values to alleviate some of the overcrowding which results from close intramolecular H...H and C...C contacts. The N-imidazolylcarbonyloxy group is nearly planar with dihedral angles of 5.2 (2) and 6.0 (2) degrees between the imidazole and carbonyl groups for molecules 1 and 2, respectively.