Synthesis of 4-Deoxy-l-(and d-)hexoses from Chiral Noncarbohydrate Building Blocks

4-Deoxy-l-hexoses were synthesized starting from our previously reported reagent 1 and (R)-benzyl glycidyl ether, which led in few steps to a substituted dihydropyran 6. The stereocontrolled hydroxylation of the latter afforded the corresponding 4-deoxy-l-hexoses 7a, 9, and 11. The same procedure, s...

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Veröffentlicht in:	Journal of organic chemistry 2004-10, Vol.69 (21), p.7033-7037
Hauptverfasser:	Caputo, Romualdo, De Nisco, Mauro, Festa, Pasquale, Guaragna, Annalisa, Palumbo, Giovanni, Pedatella, Silvana
Format:	Artikel
Sprache:	eng
Schlagworte:	Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Deoxy Sugars - chemical synthesis Epoxy Compounds - chemistry Exact sciences and technology Hexoses - chemical synthesis Organic chemistry Preparations and properties Stereoisomerism
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Beschreibung
Zusammenfassung:	4-Deoxy-l-hexoses were synthesized starting from our previously reported reagent 1 and (R)-benzyl glycidyl ether, which led in few steps to a substituted dihydropyran 6. The stereocontrolled hydroxylation of the latter afforded the corresponding 4-deoxy-l-hexoses 7a, 9, and 11. The same procedure, starting from (S)-benzyl glycidyl ether, enabled the preparation of their d-series enantiomers.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo0493774