title: Carbohydrate-based aza-macrocycles by Richman-Atkins cyclization of glucopyranose precursors.
abstract: 2, 3-Di-ω-halo- as well as 2, 3-di-ω-toluenesulfonamide-alkylated glucopyranoside derivatives were prepared. Their condensation with α,ω-bis-toluenesulfonamide components under varying Richman-Atkins conditions with alkali carbonate in DMF led to carbohydrate-linked aza-macrocycles displaying 14-, 17-, 18-, 21-, 24-, and 25-membered ring structures. Isomeric aza-macrocylic coronands of 20- as well as 30-membered ring size containing two saccharides could be obtained employing Richman-Atkins condensations of two functionalized sugar building units.
authors.affiliation: University of Hamburg, Faculty of Science, Department of Chemistry, Martin-Luther-King-Platz 6, D-20146, Hamburg, Germany.
authors.forename: Andreas
authors.initials: A
authors.lastname: Rathjens
authors.affiliation: University of Hamburg, Faculty of Science, Department of Chemistry, Martin-Luther-King-Platz 6, D-20146, Hamburg, Germany. Electronic address: thiem@chemie.uni-hamburg.de.
authors.forename: Joachim
authors.initials: J
authors.lastname: Thiem
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D043844:Crown Ethers / Q000737:chemistry*; D003500:Cyclization; D005960:Glucosides / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000737:chemistry*
chemical_list: D001372:Aza Compounds; D002241:Carbohydrates; D043844:Crown Ethers; D005960:Glucosides; D047028:Macrocyclic Compounds; D011714:Pyrans
keywords: Aza-macrocycles; Carbohydrates; Coronands; Glycophanes; Richman-Atkins cyclization