Chemoselective deprotection and functional group interconversion of ring-fused 2N,3O-oxazolidinones of N-acetyl-d-glucosamine

These studies describe the chemoselective deprotection of trans-fused 2N,3O-oxazolidinone derivatives of N-acetyl-β-d-glucosamine. Selective opening of the oxazolidinone ring or N-deacetylation without ring opening is demonstrated. Certain amines are shown to efficiently afford C-2 ureido sugars under mild conditions. This work demonstrates the high degree of chemoselective manipulation possible with ring-fused 2N,3O-oxazolidinone derivatives of N-acetyl-d-glucosamine.