Facile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranosides from ManNAc-oxazoline

• Karel Křenek,
• Petr Šimon,
• Lenka Weignerová,
• Barbora Fliedrová,
• Marek Kuzma and
• Vladimír Křen

Beilstein J. Org. Chem. 2012, 8, 428–432, doi:10.3762/bjoc.8.48

• yielding a separable mixture of the o- and p-nitrophenyl derivative in a 2:3 ratio. Keywords: α-ManNAc; glycosidase; glycosylation; nitrophenyl; oxazoline; Introduction Hexosamines are fundamental structural elements and precursors of the peptidoglycan and membrane lipopolysaccharide layer as well as of

• -α-D-mannopyranoside (8) usable as practical chromogenic substrates for the screening of such enzymes. Results and Discussion The first reported preparation of p-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside (pNP-α-ManNAc, 8) was described in [6], starting from 2-acetamido-2-deoxy-D-glucose and

• providing the product in 2% overall yield. We have previously published [7] a 9-step synthesis of pNP-α-ManNAc (8) from commercially available methyl α-D-glucopyranoside with an overall yield of 1.5%. Later, Popelová et al. [8] published a concise synthesis starting either from D-glucose (5 steps, 1.5