Synthesis and enantiomeric recognition studies of a novel 5,5-dioxophenothiazine-1,9 bis(thiourea) containing glucopyranosyl groups

A novel optically active 5,5-dioxophenothiazine-1,9 bis(thiourea) containing glucopyranosyl groups was synthesized and its enantiomeric recognition properties were examined towards the enantiomers of tetrabutylammonium salts of chiral α-hydroxy and N-protected α-amino acids using UV–vis spectroscopy.

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N,N′-[(3,7-Di-tert-butyl-5,5-dioxo-5,10-dihydro-5λ6-phenothiazine-1,9-diyl)bis(azanediylcarbonothioyl)]bis(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosylamine)C50H65N5O20S3Ee > 97%[α]D28=+75.3 (c 1.23, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (1R,2R,3S,4R,5R,1′R,2′R,3′S,4′R,5′R)

(2S)-[(2,2-Dimethylpropanoyl)amino](phenyl)acetic acidC13H17NO3Ee > 97%[α]D25=+157 (c 1.0, MeOH)Source of chirality: (S)-phenylglycineAbsolute configuration: (2S)