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The use of other liophilic promoters such as HgBr2,31 AgClO4 and AgTfO32 makes it possible to carry out the reaction with even less reactive halides. However, the stereoselective outcome of the glycosylation is very dependent not only on the reactivity of the catalyst, but also on the reactivity of both the halide and the acceptor. Careful adjustment of the reactivity of the two different components is essential in order to obtain satisfactory results. This procedure has proven to be very useful for derivatives with D-gluco, 12,33 D-galacto and L-fuco configuration.
The participation of solvents plays an important role. The use of non-polar solvents, favours the glycosylation reaction to follow a SN2-like 36 | Carbohydr. , 2009, 35, 33–70 This journal is c The Royal Society of Chemistry 2009 pathway. Under SN1-type conditions, the participation of solvents can markedly improve the stereoselectivity in glycosylation of donors with non-assisting functionalities. In diethyl ether or THF as solvents and using strong acid promoters, the solvent participates forming equatorial oxonium cations due to the reverse anomeric effect,12,22 which favours thermodynamically stable a-glycosides.
1 Nitronate addition followed by conversion to cyanides. Ko¨ll and co-workers88 have proposed a route to 1,2-cis-furanosyl cyanides (61 and 62) based on the nitromethanation of D-ribose and D-xylose, followed by dehydration and peracetylation of the 2,5-anhydro-1-deoxy-1-nitropentitol 58. Reaction with PCl3 in pyridine and subsequent acid treatment gives 3,4,6-tri-O-acetyl-a-D-altrononitrile (61a) and 3,4,6-tri-O-acetyl-a-Dgulononitrile (61b) (Scheme 21). 2 Adition of Grignard reagents. Reaction of 2,3-O-isopropylidene-Dribose (62) with ethynyl magnesium bromide gives 1,2-dideoxy-4,5-O-isopropylidene-D-allo-hept-1-ynitol (63), which is then converted into its 7-O-trityl ether (64).