Issue 3, 2017

Selective anomeric acetylation of unprotected sugars in water

Abstract

High yielding selective acetylation of only the anomeric hydroxyl of unprotected sugars is possible in aqueous solution using 2-chloro-1,3-dimethylimidazolinium chloride (DMC), thioacetic acid, and a suitable base. The reaction, which may be performed on a multi-gram scale, is stereoselective for sugars that possess a hydroxyl group at position-2, exclusively yielding the 1,2-trans products. The use of an iterative reagent addition procedure allows the use of sodium carbonate as the base, avoiding the formation of triethylammonium salts, which may hamper product purification. The glycosyl acetate products may be used as donor substrates for glycosidase-catalysed synthesis. The crude aqueous acetylation reaction mixture may also be used for this purpose.

Graphical abstract: Selective anomeric acetylation of unprotected sugars in water

Supplementary files

Article information

Article type
Edge Article
Submitted
19 Oct 2016
Accepted
09 Nov 2016
First published
11 Nov 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2017,8, 1896-1900

Selective anomeric acetylation of unprotected sugars in water

D. Lim and A. J. Fairbanks, Chem. Sci., 2017, 8, 1896 DOI: 10.1039/C6SC04667C

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