Toward the creation of NMR databases in chiral solvents for assignments of relative and absolute stereochemistry: proof of concept.
[structure: see text] An NMR database approach in a chiral solvent allows us to predict both relative and absolute stereochemistry of an unknown compound without degradation and/or derivatization. N,alpha-Dimethylbenzylamine (DMBA) is a suitable solvent for this purpose. Using the C.5-C.10 portion of oasomycin A, the feasibility and reliability of this approach is demonstrated.
Kobayashi
Y
Y
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA.
Hayashi
N
N
Tan
C H
CH
Kishi
Y
Y
D000900:Anti-Bacterial Agents / Q000737:chemistry*; D001596:Benzylamines / Q000737:chemistry*; D002384:Catalysis; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D016208:Databases, Factual; D018942:Macrolides; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012997:Solvents; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D001596:Benzylamines; D018942:Macrolides; D012997:Solvents; C410709:oasomycin; C045966:N-benzyl-N,N-dimethylamine