Generalising a Simple Methodology for the Regioselective Anomeric Deacetylation of Carbohydrates

Mitchell Hattie, Keith A. Stubbs

ChemistrySelect · 2020 · 10.1002/slct.201904343

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Abstract

The use of methylamine to deprotect 1‐ O ‐acetyl protected carbohydrates has only attracted limited interest in the literature. Demonstrated here is an approach that is able to be generalized for a wide variety of carbohydrate scaffolds which results in a high yielding, simplified, practical, expedient and clean method to prepare hemiacetals from 1‐ O ‐acetyl protected carbohydrates.

★ 5.0 1 rating
5 : Major extension (new functional group) ×1
4 : Minor extension (no new functional group) –
3 : Reproduced as published –
2 : Reproduced with deviation –
1 : Did not work –
– : Extension failed / Inconclusive –

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Industry / CRO chemist
09 Aug 2026
★ 5 : Major extension (new functional group)

This is an excellent method for deacetylation of the anomeric hydroxyl group. In our case, since the molecule contained a polar moiety, the final product was partially soluble in water. Therefore, we concentrated the crude reaction mixture directly and purified it by column chromatography, without performing an aqueous work-up beforehand. The reaction provided a fairly satisfactory yield, above 70%.