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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
- Source :
-
Carbohydrate Research . Jul2006, Vol. 341 Issue 10, p1764-1769. 6p. - Publication Year :
- 2006
-
Abstract
- Abstract: 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. [Copyright &y& Elsevier]
- Subjects :
- *GLYCOSIDES
*GLUCOSIDES
*ENZYMES
*CHROMATOGRAPHIC analysis
Subjects
Details
- Language :
- English
- ISSN :
- 00086215
- Volume :
- 341
- Issue :
- 10
- Database :
- Academic Search Index
- Journal :
- Carbohydrate Research
- Publication Type :
- Academic Journal
- Accession number :
- 21079743
- Full Text :
- https://doi.org/10.1016/j.carres.2005.12.009