title: 3-(Dimethylamino)-1-propylamine: a cheap and versatile reagent for removal of byproducts in carbohydrate chemistry.
abstract: Inexpensive 3-(dimethylamino)-1-propylamine (DMAPA) was found to be effective in anomeric deacylation reactions giving 1-O deprotected sugars in high yield as precursors for the formation of imidate glycosyl donors. DMAPA was also found to be useful for removing excess reagents such as benzoyl chloride, tosyl chloride, and 2,2,2-trifluoro-N-phenylacetimidoyl chloride. The deacylation reaction could be conducted in moist THF and did not require chromatographic purification since an acidic wash was sufficient to remove excess reagent and the formed byproduct.
authors: Department of Chemistry, Aarhus University , Langelandsgade 140, DK-8000, Aarhus C, Denmark.
authors: Sofie Meng
authors: SM
authors: Andersen
authors: Mads
authors: M
authors: Heuckendorff
authors: Henrik H
authors: HH
authors: Jensen
mesh_terms: D001565:Benzoates / Q000737:chemistry; D002241:Carbohydrates / Q000138:chemical synthesis / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003959:Diamines; D007202:Indicators and Reagents; D015394:Molecular Structure; D011437:Propylamines / Q000737:chemistry*; D014105:Tosyl Compounds / Q000737:chemistry
chemical_list: D001565:Benzoates; D002241:Carbohydrates; D003959:Diamines; D007202:Indicators and Reagents; D011437:Propylamines; D014105:Tosyl Compounds; C025506:4-toluenesulfonyl chloride; C012928:3-dimethylaminopropylamine; C013409:benzoyl chloride