Synthesis of lactoside glycodendrons using photoaddition and reductive amination methodologies.
Carbohydrate-based divalent and tetravalent lactoside glycodendrons were constructed in a convergent manner. The dendrons were synthesized beginning with the photoaddition of hepta-O-acetyl-1-thio-beta-lactose, in an anti-Markovnikov manner, to a bis-allyl AB2 trisaccharide to form a divalent dendron. Following two nearly quantitative deprotection steps, the divalent lactoside was coupled to another AB2 trisaccharide by reductive amination to afford a tetravalent dendron. These paucivalent compounds were characterized by NMR spectroscopy and mass spectrometry.
Department of Chemistry and Biochemistry, California NanoSystems Institute, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, CA 90095, USA.
Alshakim
A
Nelson
J Fraser
JF
Stoddart
D000586:Amination; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D005690:Galactose / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects*; D006027:Glycosides / Q000737:chemistry* / Q000528:radiation effects*; D008969:Molecular Sequence Data; D010084:Oxidation-Reduction; D010777:Photochemistry
D002241:Carbohydrates; D006027:Glycosides; C008245:lactosides; D005690:Galactose