A highly concise preparation of O-deacetylated arylthioglycosides of N-acetyl-D-glucosamine from 2-acetamido-3,4,6-tri-O-acetyl2-deoxy-a-D-glucopyranosyl chloride and aryl thiols or disulfides

Peer reviewed: 
Yes, item is peer reviewed.
Scholarly level: 
Faculty/Staff
Final version published as: 

Stubbs, Keith & Macauley, Matthew & Vocadlo, David. (2006). 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. Carbohydrate research. 341. 1764-9. https://doi.org/10.1016/j.carres.2005.12.009

Date created: 
2006-07-01
Identifier: 
DOI: 10.1016/j.carres.2005.12.009
Keywords: 
Thioglycoside
Phase transfer reaction
Disulfides
Arylthiols
One-pot synthesis
Enzyme substrate
Enzyme inhibitor
Abstract: 

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.

Language: 
English
Document type: 
Article
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Rights remain with the authors.
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Sponsor(s): 
Natural Sciences and Engineering Research Council of Canada (NSERC)
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