Total syntheses of enantiomerically pure D- and L-glycosyl donors as components of sannamycin-type aminoglycoside antibiotics
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 19,p. 2685-2701
- https://doi.org/10.1039/p19940002685
Abstract
Both enantiomers of purpurosaminides C (ent-7b, 13a–c), of a 2-azido analogue (ent-16b) and of 2-azido epimers (ent-26b, ent-29b), suitably protected for their direct use as glycosyl donors, are prepared from racemic 3,4-dihydro-2H-pyran-2-carbaldehyde (acrolein dimer, rac-1). The latter has been resolved on a preparative scale through the diastereoisomeric trifluoroacetylated 1′-amines obtained with (1R)- and (1S)-1-phenylethylamine, which allowed the combination of optical resolution with the introduction of the glycosyl 6-amino function.Keywords
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