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The specific deamidation of 2-acetamido-1,3,4,6-tetra-O-acetyl-α-d-glucopyranose is achieved by p-toluenesulfonic acid-promoted hydrolysis of 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-d-glucopyrano)-[2,1-d]-2-oxazoli ne2 to give quantitative formation of the 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-α-d-glucopyranosep -toluenesulfonate (5d). This two-step procedure provides an amino sugar which may...
The Me 3 SiOTf-promoted formation of GlcNAc 1,2-cis oxazoline from GlcNAc peracetates can give significant amounts of nonpolar by-products. We identified these by-products to be C-silylated esters and amides. Secondary amides are readily C-silylated by treatment with a mixture of Me 3 SiOTf and NEt 3 . These C-silylated secondary amides are useful, as they undergo fluoride...
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