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Acetyl Perchlorate Mediated Rearrangement of Tri-O-benzyl-d-glucal. Evidence for a 1,6-Hydride Shift

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Byerley, A. L. J., Kenwright, A. M., Lehmann, C. W., MacBride, J. A., & Steel, P. G. (1998). Acetyl Perchlorate Mediated Rearrangement of Tri-O-benzyl-d-glucal. Evidence for a 1,6-Hydride Shift. The Journal of Organic Chemistry, 63(1), 193-194. doi:10.1021/jo971400g.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0024-6CD7-1
Abstract
The Lewis acid mediated reaction of glycals with nucleophiles, the Ferrier reaction (Scheme 1, 1 to 3), has seen widespread use in the synthesis of glycosidic bonds. In the absence of an external nucleophile the glycal, itself, can function as the nucleophile albeit, normally, with only moderate efficacy. We have recently reported that, on treatment with acetyl perchlorate, 3-O-acyl glycals undergo an efficient dimerization leading to C-disaccharides. Here we report that attempts to use the more nucleophilic tri-O-benzyl-D-glucal 1b in this process results in an unprecedented rearrangement via a 1,6 hydride shift.