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Structural corroboration of two important building blocks of the anticancer drug eribulin mesylate through two-dimensional NMR and single-crystal X-ray diffraction studies.
- Source :
-
Acta Crystallographica Section C: Structural Chemistry . Jan2016, Vol. 72 Issue 1, p14-20. 7p. - Publication Year :
- 2016
-
Abstract
- 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 (2 R,3 R,4 R,5 S)-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. [ABSTRACT FROM AUTHOR]
- Subjects :
- *ERIBULIN
*STEREOCHEMISTRY
*X-ray diffraction
Subjects
Details
- Language :
- English
- ISSN :
- 20532296
- Volume :
- 72
- Issue :
- 1
- Database :
- Academic Search Index
- Journal :
- Acta Crystallographica Section C: Structural Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 112193960
- Full Text :
- https://doi.org/10.1107/S2053229615022305