Fast, mild, and convenient procedures for iodination and bromination of carbohydrates: reactions of organoboranes with iodine monochloride, sodium iodide, bromine, and bromine chloride
- 15 August 1982
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 60 (16) , 2082-2086
- https://doi.org/10.1139/v82-296
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).This publication has 3 references indexed in Scilit:
- Syntheses of organic iodides via reaction of organoboranes with sodium iodideThe Journal of Organic Chemistry, 1981
- RAPID AND MILD SYNTHESES OF RADIOIODINE-LABELED RADIOPHARMACEUTICALS1981
- RADIOIODINATED ESTROGEN DERIVATIVES1980