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1 article(s) from Tichá, Iveta

Enhanced single-isomer separation and pseudoenantiomer resolution of new primary rim heterobifunctionalized α-cyclodextrin derivatives

Iveta Tichá,
Gábor Benkovics,
Milo Malanga and
Jindřich Jindřich

Beilstein J. Org. Chem. 2018, 14, 2829–2837, doi:10.3762/bjoc.14.261

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Figure 1: Schematic representation of native α-CD (1) and top view of its primary rim with alphabetic clockwi...

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Scheme 1: Synthesis of 6^A,6^X-diazido-α-CD derivatives 4 via 6^A,6^X-capped α-CDs 2 and 3 and their regioisomeri...

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Scheme 2: Synthesis of 6^A,6^X- and 6^A,6^D-diazido-α-CDs via 6^A,6^X-dibromo-α-CD 5, 6^A,6^D-dibromo-α-CD 5d interme...

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Scheme 3: Synthesis of 6^A,6^X-diazido-α-CDs via 6^A,6^X-ditosyl-α-CD intermediates 6 and their regioisomeric rat...

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Figure 2: HPLC chromatograms of 6^A,6^X-diazido-α-CDs 4 of the reactions 1–5, with ACN/water gradient elution a...

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Scheme 4: Synthesis of 6^A-azido-6^X-mesitylenesulfonyl-α-CD 8 and conversion into 6^A,6^X-diazido-α-CD 4.

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Figure 3: HPLC chromatograms of reaction 7 with separated 6^A-azido-α-CD 7 as starting material and regioisome...

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Figure 4: HPLC chromatograms of 6^A-azido-6^X-mesitylenesulfonyl-α-CD 8 (reaction 6): a) analytical and b) prep...

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Figure 5: ¹H NMR spectrum of the AC regioisomer 8c as a mixture of pseudoenantiomers prepared through reactio...

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Figure 6: ¹³C NMR spectrum of the AC regioisomer 8c as a mixture of pseudoenantiomers prepared through reacti...

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Figure 7: HPLC–MS chromatogram with the separated pseudoenantiomers of 6^A-azido-6^B-mesitylenesulfonyl-α-CD 8b...

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Published 13 Nov 2018

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