Protecting an amine as a carbamate therefore enables other functional groups to undergo selective reactions with electrophiles whereby the carbamate (protected amino group) is left intact. Levulinate is an important hydroxyl protecting group in carbohydrate chemistry but has not previously been so employed in cellulose chemistry, perhaps because of challenges involved in synthesis of cellulose levulinates. 250 At the same time, these esters are stable under acidic conditions which remove the chloroacetyl, Fmoc, and silyl protecting groups. Macromolecules.

An alcohol protecting group applicable to some nucleosides. “Levulinic acid is one of the world’s most versatile building blocks for substituting oil-based products,” explained Marcel van Berkel, Chief Commercial Officer of GFBiochemicals. The levulinate esters become more and more widely used in oligosaccharide syntheses, and the reason for this is the possibility of their selective cleavage with hydrazine acetate in the presence of acetates, benzoates, and even the more sensitive chloroacetates.
The introduction of the levulinyl group was performed by esterifyingl levulinic acid with the hydroxy function of a suitably protected sugar derivative in the presence of 2-chloro-1-methyl pyridinium iodide (CMPI) and triethylamine (TEA) as the tertiary base.

Cross-Linked Sulfonated Poly (arylene ether sulfone) Membranes Formed by in Situ …

Hassner A, Strand G, Rubenstein M, Patchornik A. Cyanohydrin as an Anchoring Group for Potent and Selective Inhibitors of Enterovirus 71 3C Protease. The fast, selective and mild removal of levulinoyl groups with hydrazine from galactose, which also carries hydroxyl functions protected with acetyl groups, enabled us, under Koenigs‐Knorr conditions, to synthesize tri‐ and tetrasaccharides containing β‐linked galactose and glucose units. The fast, selective and mild removal of levulinoyl groups with hydrazine from galactose, which also carries hydroxyl functions protected with acetyl groups, enabled us, under Koenigs‐Knorr conditions, to synthesize tri‐ and tetrasaccharides containing β‐linked galactose and glucose units.

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