Glucosamine derivative 4 is a widely used precursor for syntheses of glucosamine-containing building blocks. A wide range of O-, S- and N-glycosides can be obtained from 4 under Lewis acid catalysis using the corresponding alcohols, thiols, or nitrogenous bases as nucleophiles. Since α-anomer of 4 shows much lower reactivity under these conditions, the use of pure β-anomer of 4 rather than anomeric mixture is preferred. Compound 4 is also a versatile substrate for generating the corresponding glycosyl halides under mild conditions.
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Chapter 31: A Facile Synthesis of 1,3,4,6-Tetra-O-acetyl-2-deoxy-2-trifluoroacetamido-β-d-glucopyranose, By Nikita M. Podvalnyy, Yakov V. Voznyi, Alexander I. Zinin, Polina I. Abronina, Leonid O. Kononov, and Salvatore G. Pistorio
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