期刊
JOURNAL OF CARBOHYDRATE CHEMISTRY
卷 20, 期 5, 页码 359-374出版社
MARCEL DEKKER INC
DOI: 10.1081/CAR-100105710
关键词
N-acetylneuraminic acid; sialosyl donor; ulosonic acids; glycal; halohydroxylation
Bromohydroxylation of some 4-N-acylated derivatives of the glycals of N-acetylneuraminic acid, methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate (4) and methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-talo-non-2- enonate (the 4-epimer of 4), with N-bromosuccinimide (NBS) and water in the presence of a co-solvent has provided a range of new glycosyl donors. The stereoselectivity of the halohydroxylation reaction was found to be governed by solvent composition, reaction temperature and the stereo electronic nature of the substituent at C-4.
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