Steinacher, M., Svatunek, D., Weil, M., Mohammadi, B., & Gärtner, P. (2022). Synthesis and conformational analysis of a potentially super-armed glucuronidation donor. Monatshefte Für Chemie - Chemical Monthly. https://doi.org/10.1007/s00706-022-03009-4
E163-03-3 - Forschungsgruppe Stereoselektive und nachhaltige Chemie
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Journal:
Monatshefte für Chemie - Chemical Monthly
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ISSN:
0026-9247
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Date (published):
10-Dec-2022
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Number of Pages:
6
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Publisher:
SPRINGER WIEN
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Peer reviewed:
Yes
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Keywords:
Carbohydrates; Conformation; Crystal structure; Protecting groups
en
Abstract:
The concise synthesis of a potentially “super-armed” glucuronidation donor is reported. The α-anomer was crystallized and analyzed by single crystal X-ray diffraction. The pyranose ring was found to be in a twist-boat conformation in the solid state. To confirm the relevance of this finding for the solution state, and explain the failure of analysis by NMR, DFT calculations were performed. They revealed the twist-boat to be the dominant among a group of several possible conformers at ambient temperature.
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