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O'Brien, JL,Tosin, M,Murphy, PV
2001
October
Organic Letters
Novel synthesis of the glycosidase inhibitor deoxymannojirimycin and of a synthetic precursor D-lyxo-hexos-5-ulose
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ASYMMETRIC-SYNTHESIS IN-SITU CYCLIZATION AZASUGARS (+)-1-DEOXYNOJIRIMYCIN 1-DEOXYMANNOJIRIMYCIN BIOSYNTHESIS SUGARS ENTRY
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[GRAPHICS]The synthesis Of D-lyxo-hexos-5-ulose (5-ketomannose, 1,5-dicarbonyl sugar), a synthetic precursor to the glycoprocessing inhibitor deoxymannojirimycin, was carried out by an in situ epoxidation and hydrolysis of a trimethylsilyl-protected 6-deoxyhex-5-enopyranoside followed by facile removal of the protecting groups. A novel nine-step synthesis of deoxymannojirimycin has also been achieved from methyl alpha -D-mannopyranoside; this involved methanolysis of epoxides derived from an acetylated 1-azido-6-deoxyhex-5-enopyranoside followed by deprotection and catalytic hydrogenation.
DOI 10.1021/ol016596s
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