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.
Nelson
Alshakim
A
Department of Chemistry and Biochemistry, California NanoSystems Institute, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, CA 90095, USA.
Stoddart
J Fraser
JF
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