Synthesis of urea-tethered disaccharides in water.
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.
Ichikawa
Yoshiyasu
Y
Faculty of Science, Kochi University, Akebono-cho, Kochi 780-8520, Japan. ichikawa@cc.kochi-u.ac.jp
Matsukawa
Yohei
Y
Tamura
Mari
M
Ohara
Fumiyo
F
Isobe
Minoru
M
Kotsuki
Hiyoshizo
H
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*
D023303:Oxazolidinones; D014867:Water; D002475:Cellobiose; D014508:Urea; D007785:Lactose