Stereoisomeric flavor compounds, part LVIII: The use of heptakis(2,3‐di‐O‐methyl‐6‐O‐tert‐butyldimethylsilyl)‐β‐cyclodextrin as a chiral stationary phase in flavor analysis

Abstract

The characteristics of the new chiral stationary phase heptakis(2,3-di-O-met hyl-6-0-tert-butyldimethylsilyl)-fl-cyclodextrin are outlined and compared with permethyl-and perethyl-P-cyclodextrins. Column C: . T b 7 20 25 min. 20 25 min.Figure 6 Separation of the enantiomers of lavandulyl acetate on columns A and C (coated with 15 and 5 0 % of DIME-6-TBDMS-P-CD in OV-1701-vi, respectively): conditions as for Figure 3.phases. Figure 7 shows a test for chiral GC separations on a micro preparative scale, the separation of 1-(2-methoxypheny1)ethanol on a 0.54 mm i.d. fused silica wide bore column. In this instance SE-52 was used as solvent for the modified cyclodextrin. ConclusionThe introduction of the bulky TBDMS groups slightly changes, but does not reduce, the chiral selectivity, and it is, furthermore, evident that the chiral selectivity and versatility of this new chiral stationary phase are at least as high as those of PME-P-CD.

Contributions to the theory and practice of the chromatographic separation of enantiomers

“…The dilution in polysiloxanes of the versatile derivatized cyclodextrins containing n-pentyl groups and polar acyl groups developed by König et al 61 and Armstrong et al 62 such as octakis(3-O-butanoyl-2,6-di-O-n-pentyl)-g-cyclodextrin, Lipodex E 63 7 (cf. Chart 3), originally used undiluted, as well as a second generation of cyclodextrins containing bulky 6-O-tert-butyldimethylsilyl (TBDMS) groups 64 further extended the scope of enantiomeric separation by GC, and the dilution approach is commercialized by leading column manufacturers. Various practical applications in enantiomeric analysis have been summarized.…”

Enantiomeric composition of the polycyclic musks HHCB and AHTN in different aquatic species

“…34 In an investigation of the relationship of the different stereoisomers and the musky odor of HHCB, Frater et al 31 found that the (4S,7RS)-isomers (substances 6 in Fig. 1) are powerful musky components.…”

Enantioselective synthesis and teratogenicity of propylisopropyl acetamide, a CNS-active chiral amide analogue of valproic acid

“…Separation was achieved on a capillary column (10 m, 0.25 mm, 0.25 µm) coated with Heptakis-(2,3-di-O-methyl-6-Otert-butyldimethylsilyl)-␤-cyclodextrin as the stationary phase. 15,16 The Carrier gas was nitrogen, column head pressure 50 KPa, split ratio 1:30, injector 250°C, detector 300°C and column temperature 120°C isothermal.…”