title: Synthesis of urea-tethered disaccharides in water.
abstract: A new method for the synthesis of urea-linked disaccharides in aqueous media has been developed. The key feature of our approach is two strained Steyermark-type gluco- and galactopyranosyl oxazolidinones. Each oxazolidinone is attached to a pyranose ring in a di-equatorial trans-annulation framework. Reaction of these oxazolidinones with 4-aminohexopyranose in water proceeded smoothly to afford the urea-tethered cellobiose and lactose analogues. The galactose-type oxazolidinone proved to be more reactive than the glucose-type, which is explained by the presence of an axial hydroxy group at C4 in the former.
authors: Faculty of Science, Kochi University, Akebono-cho, Kochi 780-8520, Japan. ichikawa@cc.kochi-u.ac.jp
authors: Yoshiyasu
authors: Y
authors: Ichikawa
authors: Yohei
authors: Y
authors: Matsukawa
authors: Mari
authors: M
authors: Tamura
authors: Fumiyo
authors: F
authors: Ohara
authors: Minoru
authors: M
authors: Isobe
authors: Hiyoshizo
authors: H
authors: Kotsuki
mesh_terms: D002475:Cellobiose / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D006031:Glycosylation; D007785:Lactose / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D023303:Oxazolidinones / Q000737:chemistry; D014508:Urea / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
chemical_list: D023303:Oxazolidinones; D014867:Water; D002475:Cellobiose; D014508:Urea; D007785:Lactose