Eribulin mesylate, one of the most synthetically challenging drugs to date, possesses 19 stereocentres in its structure and ascertaining the absolute stereochemistry at every stage of the 64-stage synthesis is crucial. In our quest to synthesize eribulin, we identified two critical building blocks of this molecule, namely 3,4:6,7-di-O-cyclohexylidene-d-glycero-α-l-talo-heptopyranose methanol monosolvate, C19H30O7·CH3OH, and (2R,3R,4R,5S)-5-allyl-2-[(S)-2,3-dihydroxypropyl]-4-[(phenylsulfonyl)methyl]tetrahydrofuran-3-ol, C17H24O6S, for which two-dimensional NMR (2D-NMR) data were not sufficient to prove the absolute configuration. To ensure structural integrity, single-crystal X-ray diffraction data were obtained to confirm the structures. This information provides useful insights into the structural framework of the large eribulin mesylate molecule.
|Original language||English (US)|
|Number of pages||7|
|Journal||Acta Crystallographica Section C: Structural Chemistry|
|State||Published - 2016|
Bibliographical notePublisher Copyright:
© 2016 International Union of Crystallography.
- anticancer drug
- asymmetric dihydroxylation
- crystal structure
- double stereodiffrentiation
- eribulin mesylate
- Halichondrin B
- Karplus equation
- two-dimensional NMR