Bromohydroxylation of glycals - An investigation into the reaction of some4-N-acylated derivatives of methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate and its 4-epimer
Gb. Kok et al., Bromohydroxylation of glycals - An investigation into the reaction of some4-N-acylated derivatives of methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate and its 4-epimer, J CARB CHEM, 20(5), 2001, pp. 359-374
Bromohydroxylation of some 4-N-acylated derivatives of the glycals of N-ace
tylneuraminic 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 (t
he 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 stereosele
ctivity of the halohydroxylation reaction was found to be governed by solve
nt composition, reaction temperature and the stereo electronic nature of th
e substituent at C-4.