Journal of Carbohydrate Chemistry p. 359 - 374 (2001)
Update date:2022-09-26
Topics:
Kok, Gaik B.
Van Phan, Tho
Von Itzstein, Mark
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-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-no n-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 stereoelectronic nature of the substituent at C-4.
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