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Application of the Bichromophoric Exciton Chirality Method to the Stereochemical Elucidation of Acyclic Polyols

William T. Wiesler ; Department of Chemistry, Columbia University, New York, NY 10027, U.S.A.
Koji Nakanishi ; Department of Chemistry, Columbia University, New York, NY 10027, U.S.A.

Sažetak

The recently developed technique of bichromophoric derivatization
extends the utility of the exciton chirality method.
Selective introduction of two types of exciton chromophores to
two different types of hydroxyl groups gives rise to highly
characteristic CD curves. Pairs of chromophores are evaluated for
two different applications: 1) an oligosaccharide linkage analysis,
and 2) elucidation of stereochemistry in acyclic polyhydroxyl compounds with two or more stereocenters. For the latter application,
selective introduction of the 9-anthroate chromophore (lemax = 253
nm) at prirnary hydroxyls, together with the p-methoxycinnamate
chromophore (,1,m" = 311 nm) introduced at secondary hydroxyls of
stereocenters, gives rise to highly characteristic CD spectra. Examination by this method of all diastereomeric n-tetrose and n-peritose diethyl dithioacetals indicates that the anthroate/methoxycinnamate bichromophoric approach is a promising method for assignment of stereochemistry in 1,2,3-triols, 1,2.3,4-tetrols,and other polyhydroxylated compounds.

Ključne riječi

Hrčak ID:

175394

URI

https://hrcak.srce.hr/175394

Datum izdavanja:

30.6.1989.

Posjeta: 927 *