A highly concise preparation of O-deacetylated arylthioglycosides of N-acetyl-D-glucosamine from 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-glucopyranosyl chloride and aryl thiols or disulfides.
An expedient and mild route to a range of aryl 2-acetamido-2-deoxy-1-thio-beta-D-glucopyranosides has been devised from 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-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.
Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, BC, Canada V5A 1S6.
Keith A
KA
Stubbs
Matthew S
MS
Macauley
David J
DJ
Vocadlo
D000117:Acetylglucosamine / Q000031:analogs & derivatives / Q000737:chemistry*; D004220:Disulfides / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013865:Thioglycosides / Q000138:chemical synthesis*
D004220:Disulfides; D013438:Sulfhydryl Compounds; D013865:Thioglycosides; D000117:Acetylglucosamine