Addition of trialkylaluminum reagents to glyconolactones. Synthesis of 1-C-methyl GlcNAc oxazoline and thiazoline

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Abstract

Addition of carbon nucleophiles to 2-acetamido-2-deoxygluconolactones fails for many reagents, but trialkylaluminums add alkyl smoothly. The product of methyl addition to 2-acetamido-2-deoxy-D-gluconolactone has been converted to 1-C-methyl GlcNAc thiazoline, a potential N-acetylhexosaminidase inhibitor, and to an O-protected 1-C-Me GlcNAc oxazoline, a potential 1-C-Me GlcNAc donor. © 2002 Elsevier Science Ltd. All rights reserved.

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Knapp, S., Yang, C., & Haimowitz, T. (2002). Addition of trialkylaluminum reagents to glyconolactones. Synthesis of 1-C-methyl GlcNAc oxazoline and thiazoline. Tetrahedron Letters, 43(39), 7101–7104. https://doi.org/10.1016/S0040-4039(02)01506-X

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