European Journal of Organic Chemistry p. 5365 - 5376 (2016)
Update date:2022-08-11
Topics:
Kristensen, Steffan K.
Salamone, Stéphane
Rasmussen, Michelle R.
Marqvorsen, Mikkel H. S.
Jensen, Henrik H.
We describe the β-ortho-methoxybenzoate as a shelf stable and practical C-1 nucleofuge for catalytic chemical glycosylation in which the benzoic acid by-product can be easily removed, reisolated, and potentially recycled after the glycosylation reaction. This new type of glycosyl donor can be efficiently activated by a range of promoters, including Bi(OTf)3, Fe(OTf)3, TMSOTf (TMS = trimethylsilyl), and triflic acid, with low (<10 mol-%) catalyst loadings. The donor shows higher reactivity than analogous benzoate, p-methoxybenzoate and p-cyano-o-methoxybenzoate donors. In glycosylation reactions with o-methoxybenzoate donors, the yields of disaccharide products were good to excellent for various glycosyl acceptors, including a carbohydrate-based secondary alcohol. Furthermore, β-selective mannosylation was achieved with a Crich-type donor at 0 °C to ambient temperature, without donor preactivation. The donor was also used for the first step of a one-pot two-step glycosylation to obtain a trisaccharide; the second coupling involved activation of a thioglycoside with NIS/TMSOTf (NIS = N-iodosuccinimide). We believe that this offers a good alternative to current protocols.
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