Structural corroboration of two important building blocks of the anticancer drug eribulin mesylate through two-dimensional NMR and single-crystal X-ray diffraction studies.
Acta crystallographica. Section C, Structural chemistry(2016)
摘要
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.
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关键词
COSY,Halichondrin B,Karplus equation,NOESY,anticancer drug,asymmetric dihydroxylation,crystal structure,double stereodiffrentiation,eribulin mesylate,two-dimensional NMR
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