An approach to 8 stereoisomers of homonojirimycin from (D)-glucose via kinetic and thermodynamic azido-γ-lactones.

Journal article

Crystal structures were obtained for the two C2 epimeric azido-γ-lactones 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d-glycero-d-ido-heptono-1,4-lactone and 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d-glycero-d-gulo-heptono-1,4-lactone prepared from kinetic and thermodynamic azide displacements of a triflate derived from d-glucoheptonolactone. Azido-γ-lactones are very useful intermediates in the synthesis of iminosugars and polyhydroxylated amino acids. In this study two epimeric azido-he...

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Authors: Glawar, A; Jenkinson, S; Newberry, S; Thompson, A; Nakagawa, S

• Publication status: Published
• Journal: Organic and biomolecular chemistry
• Volume: 11
• Issue: 40
• Pages: 6886-6899
• Publication date: 2013-09-01
• DOI: 10.1039/c3ob41334a
• EISSN: 1477-0539
• ISSN: 1477-0520
• Language: English
• Keywords: Azides; Stereoisomerism; Kinetics; Models, Molecular; 1-Deoxynojirimycin; Lactones; Thermodynamics; Glucose; Molecular Conformation