Stereoselective synthesis of 1,2:4,5-di-O-isopropylidene-3-C-(5-phenyl-1,2,4-oxadiazol-3-yl)-β-d-psicopyranose and its X-ray crystallographic analysis

Add time:08/30/2019    Source:sciencedirect.com

In a novel procedure, when 3-O-benzoyl-3-C-(N-hydroxycarbamimidoyl)-1,2:4,5-di-O-isopropylidene-β-d-psicopyranose (1) is treated with acetic anhydride, chloroacetyl chloride, propanic anhydride and benzoyl chloride, the 3-O-benzoyl group undergoes an intramolecular replacement reaction with neighbouring group participation and transfer resulting in a more stable conjugated system by the formation of a 1,2,4-oxadiazol ring. A possible mechanism is reported. The structure has been determined by spectroscopic data and X-ray crystallographic analysis.

We also recommend Trading Suppliers and Manufacturers of 1,2:4,5-DI-O-ISOPROPYLIDENE-BETA-D-PSICOPYRANOSE (cas 18422-54-3). Pls Click Website Link as below: cas 18422-54-3 suppliers

Prev:Exploration of chiral induction on epoxides in lipase-catalyzed epoxidation of alkenes using (2R,3S,4R,5S)-(–)-2,3:4,6-di-O-isopropylidiene-2-keto-l-gulonic acid monohydrate
Next:NoteSynthesis of branched-chain sugar derivatives from 1,2;5,6-di-O-isopropylidene-α-d-ribo-hexofuranos-3-ulose and 1,2;4,5-di-O-isopropylidene-β-d-erythro-2-hexulopyranos-3-ulose☆)