A highly concise preparation of O-deacetylated arylthioglycosides of N-acetyl-d-glucosamine from 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-d-glucopyranosyl chloride and aryl thiols or disulfides

An expedient and mild route to a range of aryl 2-acetamido-2-deoxy-1-thio-β-d-glucopyranosides has been devised from 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-d-glucopyranosyl chloride and arylthiols or aryl disulfides using phase transfer catalysis conditions. This simple procedure compresses up to three synthetic steps into a one-pot reaction, obviating the need for tedious workups and chromatography and directly furnishes crystalline materials in good yields. The procedure is compatible with a range of thiols and disulfides and may be amenable for preparing a wide range of thioglycosides with various glycons and aglycons.

Graphical abstractA direct preparation of O-deacetylated arylthioglycosides of N-acetyl-d-glucosamine from 2-acetamido-2-deoxy-1-thio-β-d-glucopyranosyl chloride and aryl thiols or disulfides.Figure optionsDownload full-size imageDownload as PowerPoint slide