The use of epoxides obtained by dimethyldioxirane epoxidation of 2,3-anhydro-1,3-dideoxy-4,5:7,8-di-O-isopropylidene-D-manno-oct-1-enitol as glycosyl donors is described. This method offers a simple and stereoselective access to precursors of Kdo glycosides. The stereochemical outcome of the reaction is rationalized by means of semiempirical calculations of the transition states leading to glycosides formation.
Synthetic approach to Kdo glycosides via exo-glycal epoxides and rationalization of the stereo chemical outcome / L. Lay, F. Nicotra, L. Panza, G. Russo, G. Sello. - In: JOURNAL OF CARBOHYDRATE CHEMISTRY. - ISSN 0732-8303. - 17:8(1998), pp. 1269-1281.
Synthetic approach to Kdo glycosides via exo-glycal epoxides and rationalization of the stereo chemical outcome
L. LayPrimo
;G. RussoPenultimo
;G. SelloUltimo
1998
Abstract
The use of epoxides obtained by dimethyldioxirane epoxidation of 2,3-anhydro-1,3-dideoxy-4,5:7,8-di-O-isopropylidene-D-manno-oct-1-enitol as glycosyl donors is described. This method offers a simple and stereoselective access to precursors of Kdo glycosides. The stereochemical outcome of the reaction is rationalized by means of semiempirical calculations of the transition states leading to glycosides formation.
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