392712-32-2Relevant academic research and scientific papers
Bromohydroxylation of glycals - An investigation into the reaction of some 4-N-acylated derivatives of methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-no n-2-enonate and its 4-epimer
Kok, Gaik B.,Van Phan, Tho,Von Itzstein, Mark
, p. 359 - 374 (2001)
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.
