G. Hodosi, B. Podányi, J. Kuszmann
Jun 16, 1992
Citations
0
Influential Citations
34
Citations
Journal
Carbohydrate Research
Abstract
Abstract Triphenylphosphine reacts with N -bromosuccinimide to give a phosphonium salt ( 13 ), which reacts with N,N -dimethylformamide to afford N,N -dimethylsuccinimidomethaniminium bromide ( 16 ). The latter product reacts with an alcohol to give an O -forminimium compound 17 , and, in the presence of an alcohol, 13 is transformed into an alkoxyphsphonium intermediate ( 14 ). Both 14 and 17 can be converted by heating into an alkyl bromide. Hydrolysis of 17 gives the corresponding O -formyl derivative. Reaction of 1.2:5.6-di- O -isopropylidene-α- d -glucofuranose with 13 or 16 gave 6-bromo-6-deoxy-1,2:3,5-di- O -isopropylidene-α- d -glucofuranose and a possible mechanism for these reactions is suggested. An efficient method for the preparation of 3-deoxy-3-halogeno-1,2:5,6-di- O -isopropylidene-α- d -allofuranose derivatives and a new procedure for selective O -formylation are described.