The ‘Ether Model’ has been widely cited in carbohydrate chemistry to explain the dominance of the alpha over the beta anomer (or 1,2-cis over 1,2-trans) selectivity in glycosylation reactions. The literature is replete with examples of 1,2-cis-selective glycosylation reactions that employ ether solvent along with activators/promoters furnishing triflate or perchlorate counteranions. This latter fact appears to be largely overlooked, and there is strong evidence that these counteranions play a non-innocent role in glycosylation. The experiments conducted in this study seek evidence for the relevance of the glycosyl oxonium ion which has been considered pivotal in favoring alpha selectivity. This study tests the veracity of the ‘Ether Model’ as an argument to explain the selectivity of the glycosylation reactions conducted in either solvents.

Examining the authenticity of the ‘ether model’ in glycosylation reactions

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