Abstract
5,6-Dideoxy-1,2-O-isopropylidene-3-O-methanesulfonyl-α-D-xlyo-hexofuranosene-5 (1), reacts with BH3–THF to form the tris(glycosyl)borane (2) and with dicyclohexylborane to form the dicyclohexylglycosylborane (3). The iodination and bromination of 2 and 3 has been investigated using a variety of electrophiles. Iodination of either 2 or 3 with NaI–Chloramine-T/NaOAc is complete within one minute with high percentage uptake of iodine (70–90%) and recovery of the iodinated sugar (4). Bromination of 2 in 15 minutes with NaBr–Chloramine-T permits a high percentage uptake of bromine (75%), and bromination of 3 in 15 minutes with Br2/NaOAc gives the brominated sugar (5) with a reasonably good yield (60%) with respect to the starting material (1).
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