Abstract
An expedient synthetic method has been developed for O-glycosidation of 3,4,6-tri- O-acetyl -D- glucal for the synthesis of 2,3-unsaturated O-glycosides using bromodimethylsulfonium bromide (BDMS) as a pre-catalyst through Ferrier rearrangement. Some of the salient features of the present protocol are mild reaction conditions, shor ter reaction time, easy work-up procedure, high α-selectivity and good yields.
Highlights
3,4,6-Tri-O-acetyl-D-glucal has been found to be useful glycosyl donor for O-glycosidic bond formation reaction in carbohydrate chemistry.[1]
Very recently we have shown the same catalyst is effective for multicomponent reaction for the synthesis of heterocyclic compounds14a as well as other organic molecules.14b,c In this paper, we would like to report the synthesis of 2,3-unsaturated-O-glycosides from 3,4,6-tri-O-acetyl-D-glucal and various alcohols in presence of BDMS as a pre-catalyst as shown in Scheme 1
To find out the optimal reaction conditions, we have chosen as 3,4,6-tri-O-acetyl-Dglucal (1) and p-bromobenzylalchol (2a) as model substrates
Summary
3,4,6-Tri-O-acetyl-D-glucal has been found to be useful glycosyl donor for O-glycosidic bond formation reaction in carbohydrate chemistry.[1]. The desired product 3a was obtained in good yield, which was characterized from 1H NMR, 13C NMR spectra and elemental analysis. To compare the efficacy with other catalysts, similar reactions were performed again with different metal triflates namely Co(OTf)[2] and Mn(OTf)[2] in acetonitrile (Table 1, entries 7 and 8), which provided the product 3a in low yield and poor selectivity.
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