Short and efficient synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-tetrahydroxyazepanes via the Henry reaction.
The Henry reaction with the easily available alpha-d-xylo-pentodialdose afforded a diastereomeric mixture of nitroaldoses with the alpha-d-gluco- and beta-l-ido-configuration, respectively, in good yield. When n-BuLi was used as the base, the reaction afforded the alpha-d-gluco-nitroaldose as the only product. The reduction of the nitro group in the alpha-d-gluco- and beta-l-ido-nitroaldoses, removal of the protecting groups and intramolecular reductive cyclo-amination afforded the corresponding (2S,3R,4R,5R) and (2S,3R,4R,5S) tetrahydroxyazepanes.
Chakraborty
Chaitali
C
Garware Research Centre, Department of Chemistry, University of Pune, Pune 411 007, India.
Dhavale
Dilip D
DD
D005947:Glucose / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D000432:Methanol / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D009595:Nitroparaffins / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013402:Sugar Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D013696:Temperature; D013997:Time Factors
D009595:Nitroparaffins; D013402:Sugar Alcohols; D005947:Glucose; D008697:Methane; C008640:nitromethane; D000432:Methanol