1,6-Anhydrofurawosen, XX.1 Synthese von Zuei 1,6:2,3-Dianhydrohexofuranosen Durch Payne-Oxidation von 1,6-Anhydro-5-O-Benzoyl-2,3-Didesoxy-β-D-Erythro- uno -α-L-Threo-Hex-2-Enofuranose
Title:
1,6-Anhydrofurawosen, XX.1 Synthese von Zuei 1,6:2,3-Dianhydrohexofuranosen Durch Payne-Oxidation von 1,6-Anhydro-5-O-Benzoyl-2,3-Didesoxy-β-D-Erythro- uno -α-L-Threo-Hex-2-Enofuranose
Author:
Koll, Peter Eisermann, Doris
Appeared in:
Journal of carbohydrate chemistry
Paging:
Volume 7 (1988) nr. 4 pages 757-771
Year:
1988-12-01
Contents:
The 5-0-benzoyl derivatives 3 and 4 derived from 1,6-anhydro-β-D-mannpfuranose and -α-L-gulofuranose are suitable educts for the preparation of the isomeric olefins 7 and 8 by Corey-Winter elimination via the thionocarbonates 5 and 6, respectively. 8 was prepared in higher yields also from 5-α-Benzoyl-1,6-anhydro-α-L-talofuranose (14) via 15. Payne oxidation of the unsaturated compounds 7 and 8 gave the exo epoxides 9 and 10 with D-allo and L-talo configuration.
Journal description