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

Abstract:

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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Publication status:
Published

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Publisher copy:
10.1039/c3ob41334a

Authors


Glawar, AF More by this author
Jenkinson, SF More by this author
Newberry, SJ More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Inorganic Chemistry
Nakagawa, S More by this author
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Journal:
Organic and biomolecular chemistry
Volume:
11
Issue:
40
Pages:
6886-6899
Publication date:
2013-09-05
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
URN:
uuid:c08e1e8a-a138-4a92-b84b-f2e135c1f972
Source identifiers:
418342
Local pid:
pubs:418342

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